Six-membered C—N-bonded aryl sulphide and aryl sulphoxide derivatives as pesticides

ABSTRACT

Illustrated are compounds of the formula (I), which are suitable for controlling animal pests including arthropods and in particular insects and acarids 
                         
in which the structural elements have the meanings given in the description.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a § 371 National Stage Application ofPCT/EP2014/077576, filed 12 Dec. 2014, which claims priority to13197460.2, filed 16 Dec. 2013.

BACKGROUND Field of the Invention

The present application relates to novel heterocyclic compounds, toprocesses for preparation thereof and to the use thereof for controllinganimal pests, which include arthropods and especially insects.

Description of Related Art

Aryl sulphide and aryl sulphoxide derivatives and their insecticidal andacaricidal action are already known, for example from WO 1999/055668 A1.Arylquinazolinones and their insecticidal and acaricidal action arealready known from WO 2010/100189 A1.

Crop protection agents, which also include pesticides, have to meet manydemands, for example in relation to efficacy, persistence, and spectrumof action and possible use. Questions of toxicity and of combinabilitywith other active compounds or formulation auxiliaries play a role, asdoes the question of the expense that the synthesis of an activecompound requires. In addition, resistances can occur. For all thesereasons, the search for novel crop protection compositions cannot beconsidered to be complete, and there is a constant need for novelcompounds having properties which, compared to the known compounds, areimproved at least in relation to individual aspects.

SUMMARY

It was an object of the present invention to provide compounds whichwiden or improve the spectrum of the pesticides in various respects.

This object, and further objects which are not stated explicitly but canbe discerned or derived from the connections discussed herein, areachieved by novel compounds of the formula (I)

in which (Embodiment 1-1)

-   V represents oxygen or represents sulphur or represents substituted    nitrogen;-   Q represents substituted carbon or represents nitrogen;-   R³ and R⁶ independently of one another represent    -   hydrogen, halogen, cyano or nitro; or    -   represent alkyl, alkenyl, alkynyl, alkoxy, alkylsulphanyl,        alkylsulphinyl, alkylsulphonyl, haloalkylcarbonyl, alkylcarbonyl        or alkoxycarbonyl, where the radicals mentioned above may        optionally be substituted; or    -   represent cycloalkyl, cycloalkylalkyl or cycloalkenyl in which        the rings may contain at least one heteroatom selected from the        group consisting of sulphur, oxygen and nitrogen, with the        proviso that two oxygen atoms must not be directly adjacent to        one another, where the radicals mentioned above may optionally        be substituted; or    -   represent aryl, heteroaryl, arylalkyl or heteroarylalkyl, where        the radicals mentioned above may optionally be substituted; or    -   represent NR′R″,        -   where R′ and R″ independently of one another represent            hydrogen, cyano, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl,            alkoxyalkyl, alkylsulphanylalkyl, alkylsulphinylalkyl,            alkysulphonylalkyl, alkenyl, haloalkenyl, cyanoalkenyl,            alkynyl, haloalkynyl, cyanoalkynyl, acyl or alkoxycarbonyl;        -   or        -   where R′ and R″ together with the nitrogen atom to which            they are attached may form an optionally substituted,            saturated or unsaturated three- to eight-membered ring            optionally interrupted by one or more heteroatoms            independently selected from the group consisting of O, S and            N, with the proviso that two oxygen atoms must not be            directly adjacent to one another; or-   W represents hydrogen or halogen;-   n represents the number 0, 1 or 2;-   Y represents hydrogen, halogen, (C₁-C₆)-alkyl, trifluoromethyl,    (C₂-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy or amino; or    -   represents NR′″R″″,        -   where R′″ and R″″ independently of one another represent            hydrogen, (C₁-C₆)-alkyl or (C₂-C₆)-haloalkyl;-   X represents hydrogen, halogen, cyano, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl or (C₁-C₆)-alkoxy.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

It has been additionally found that the novel compounds of the formula(I) have good efficacy as pesticides, for example against arthropods andespecially insects, nematodes and acarids, and additionally generallyhave very good compatibility with plants, especially crop plants, and/orhave favourable toxicological and/or environmentally relevantproperties.

Preferred substituents or ranges for the radicals shown in the compoundsof the formula (I) are illustrated below (Embodiment 2-1).

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulphanyl, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphanyl,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,    (C₃-C₆)-cycloalkyl or (C₁-C₆)-alkoxy;-   R³ and R⁶ independently of one another    -   represent hydrogen, halogen, cyano or nitro; or    -   represent (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₁-C₆)-haloalkylsulphanyl, (C₁-C₆)-haloalkylsulphinyl,        (C₁-C₆)-haloalkylsulphonyl, (C₁-C₆)-alkylsulphanyl,        (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₅)-alkylcarbonyl, (C₁-C₅)-haloalkylcarbonyl or        (C₂-C₆)-alkoxy carbonyl; or    -   represent (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₃)-alkyl        or (C₃-C₆)-cycloalkenyl, where the radicals mentioned above may        optionally be substituted by halogen, alkyl, cyano, nitro,        alkoxy, haloalkyl or haloalkoxy; or    -   represent phenyl, heteroaryl, phenyl-(C₁-C₃)-alkyl or        heteroaryl-(C₁-C₃)-alkyl, where the radicals mentioned above may        optionally be substituted by halogen, alkyl, cyano, nitro,        alkoxy, haloalkyl or haloalkoxy; or    -   represent NR′R″,        -   where R′ and R″ independently of one another represent            hydrogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,            (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy,            (C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₃-C₄)-alkenyl,            (C₃-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₃-C₄)-alkynyl,            (C₃-C₄)-haloalkynyl, (C₃-C₄)-cyanoalkynyl,            (C₁-C₄)-alkylcarbonyl or (C₁-C₄)-alkoxy carbonyl;        -   or        -   where R′ and R″ together with the nitrogen atom to which            they are attached may form an optionally halogen-, alkyl-,            cyano-, nitro-, alkoxy-, haloalkyl- or            haloalkoxy-substituted, saturated or unsaturated three- to            eight-membered ring optionally interrupted by one or more            heteroatoms independently selected from the group consisting            of O, S and N, with the proviso that two oxygen atoms must            not be directly adjacent to one another; or-   W represents hydrogen or halogen;-   n represents the number 0 or 1;-   Y represents hydrogen, halogen, (C₁-C₄)-alkyl, trifluoromethyl,    (C₂-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or amino; or    -   represents NR′″R″″,        -   where R′″ and R″″ independently of one another represent            hydrogen, (C₁-C₄)-alkyl or (C₂-C₄)-haloalkyl;-   X represents hydrogen, halogen, cyano, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl or (C₁-C₄)-alkoxy.

In a further embodiment (Embodiment 2-2), the preferred substituents orranges of the radicals given in the compounds of the formula (I) are asfollows:

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulphanyl, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphanyl,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl or    (C₁-C₆)-alkoxy;-   R³ and R⁶ independently of one another    -   represent hydrogen, halogen, cyano or nitro; or    -   represent (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₁-C₆)-haloalkylsulphanyl, (C₁-C₆)-haloalkylsulphinyl,        (C₁-C₆)-haloalkylsulphonyl, (C₁-C₆)-alkylsulphanyl,        (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₅)-haloalkylcarbonyl or (C₂-C₆)-alkoxycarbonyl; or        represent NR′R″,        -   where R′ and R″ independently of one another represent            hydrogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,            (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy,            (C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₃-C₄)-alkenyl,            (C₃-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₃-C₄)-alkynyl,            (C₃-C₄)-haloalkynyl, (C₃-C₄)-cyanoalkynyl,            (C₁-C₄)-alkylcarbonyl or (C₁-C₄)-alkoxycarbonyl;-   W represents hydrogen or halogen;-   n represents the number 0 or 1;-   Y represents hydrogen, halogen, (C₁-C₄)-alkyl, trifluoromethyl,    (C₂-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or amino; or    -   represents NR′″R″″,        -   where R′″ and R″″ independently of one another represent            hydrogen, (C₁-C₄)-alkyl or (C₂-C₄)-haloalkyl;-   X represents hydrogen, halogen, cyano, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl or (C₁-C₄)-alkoxy.

In a further embodiment (Embodiment 2-3), the preferred substituents orranges of the radicals given in the compounds of the formula (I) are asfollows:

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulphanyl, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphanyl,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,    (C₃-C₆)-cycloalkyl or (C₁-C₆)-alkoxy;-   R³ and R⁶ independently of one another    -   represent (C₁-C₅)-alkylcarbonyl; or    -   represent (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₃)-alkyl        or (C₃-C₆)-cycloalkenyl, where the radicals mentioned above may        optionally be substituted by halogen, alkyl, cyano, nitro,        alkoxy, haloalkyl or haloalkoxy; or represent phenyl,        heteroaryl, phenyl-(C₁-C₃)-alkyl or heteroaryl-(C₁-C₃)-alkyl,        where the radicals mentioned above may optionally be substituted        by halogen, alkyl, cyano, nitro, alkoxy, haloalkyl or        haloalkoxy; or    -   represent NR′R″,        -   where R′ and R″ together with the nitrogen atom to which            they are attached may form an optionally halogen-, alkyl-,            cyano-, nitro-, alkoxy-, haloalkyl- or            haloalkoxy-substituted, saturated or unsaturated three- to            eight-membered ring optionally interrupted by one or more            heteroatoms independently selected from the group consisting            of O, S and N, with the proviso that two oxygen atoms must            not be directly adjacent to one another; or-   W represents hydrogen or halogen;-   n represents the number 0 or 1;-   Y represents hydrogen, halogen, (C₁-C₄)-alkyl, trifluoromethyl,    (C₂-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or amino; or    -   represents NR′″R″″,        -   where R′″ and R″″ independently of one another represent            hydrogen, (C₁-C₄)-alkyl or (C₂-C₄)-haloalkyl;-   X represents hydrogen, halogen, cyano, (C₁-C₄)-haloalkyl or    (C₁-C₄)-alkoxy.

More preferred substituents or ranges for the radicals shown in thecompounds of the formula (I) are illustrated below (Embodiment 3-1).

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl or (C₁-C₄)-alkoxy;-   R³ and R⁶ independently of one another    -   represent hydrogen or halogen; or    -   represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or        (C₁-C₄)-haloalkoxy; or    -   represent (C₃-C₆)-cycloalkyl or        (C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl, where all of the radicals        mentioned above may optionally be substituted by fluorine,        chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro,        (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy; or    -   represent phenyl or phenyl-(C₁-C₃)-alkyl, where the radicals        mentioned above may optionally be mono- or disubstituted by        fluorine, chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano,        nitro, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy;        or    -   represent heteroaryl selected from the group consisting of        furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,        1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl,        thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,        1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,        1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl,        pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,        1,2,4-triazinyl, 1,3,5-triazinyl, indolyl, isoindolyl and        indazolyl, where the radicals mentioned above may optionally be        mono- or disubstituted by fluorine, chlorine, bromine, iodine,        (C₁-C₃)-alkyl, cyano, nitro, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl        or (C₁-C₃)-haloalkoxy; or    -   represent NR′R″,        -   where R′ and R″ independently of one another represent            hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,            (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylcarbonyl            or (C₁-C₄)-alkoxycarbonyl;        -   or        -   where R′ and R″ together with the nitrogen atom to which            they are attached may form a saturated four- to six-membered            ring which is optionally mono- or disubstituted by fluorine,            chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro,            (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy and            optionally interrupted by a heteroatom selected from the            group consisting of O, S and N;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy,    amino, methylamino or dimethylamino;-   X represents hydrogen, fluorine, chlorine, bromine, cyano, methyl,    ethyl, trifluoromethyl, methoxy or ethoxy.

In a further embodiment (Embodiment 3-2), the more preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl or (C₁-C₄)-alkoxy;-   R³ and R⁶ independently of one another    -   represent hydrogen or halogen; or    -   represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or        (C₁-C₄)-haloalkoxy; or    -   represent NR′R″,        -   where R′ and R″ independently of one another represent            hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,            (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,            (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylcarbonyl            or (C₁-C₄)-alkoxycarbonyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy,    amino, methylamino or dimethylamino;-   X represents hydrogen, fluorine, chlorine, bromine, cyano, methyl,    ethyl, trifluoromethyl, methoxy or ethoxy.

In a further embodiment (Embodiment 3-3), the more preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵ or nitrogen, where-   R⁵ represents hydrogen, halogen, amino, cyano, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl or (C₁-C₄)-alkoxy;-   R³ and R⁶ independently of one another    -   represent (C₃-C₆)-cycloalkyl or        (C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl, where the radicals mentioned        above may optionally be substituted by fluorine, chlorine,        bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro, (C₁-C₃)-alkoxy,        (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy; or    -   represent phenyl or phenyl-(C₁-C₃)-alkyl, where the radicals        mentioned above may optionally be mono- or disubstituted by        fluorine, chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano,        nitro, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy;        or    -   represent heteroaryl selected from the group consisting of        furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,        1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl,        thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,        1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,        1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl,        pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,        1,2,4-triazinyl, 1,3,5-triazinyl, indolyl, isoindolyl and        indazolyl, where the radicals mentioned above may optionally be        mono- or disubstituted by fluorine, chlorine, bromine, iodine,        (C₁-C₃)-alkyl, cyano, nitro, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl        or (C₁-C₃)-haloalkoxy; or    -   represent NR′R″,        -   where R′ and R″ together with the nitrogen atom to which            they are attached may form a saturated four- to six-membered            ring which is optionally mono- or disubstituted by fluorine,            chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro,            (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy and            optionally interrupted by a heteroatom selected from the            group consisting of O, S and N;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy,    amino, methylamino or dimethylamino;-   X represents hydrogen, fluorine, chlorine, bromine, cyano, methyl,    ethyl, trifluoromethyl, methoxy or ethoxy.

Particularly preferred substituents or ranges for the radicals shown inthe compounds of the formula (I) are illustrated below (Embodiment 4-1).

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen, methyl, ethyl, methoxy, cyclopropyl or    trifluoromethyl;-   R³ and R⁶ independently of one another represent hydrogen, methyl,    ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl,    cyclopropyl or phenyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or    methoxy;-   X represents hydrogen, chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F),        (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H),        (CF₃,F).

In a further embodiment (Embodiment 4-2), the particularly preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen, methyl, ethyl or trifluoromethyl;-   R³ and R⁶ independently of one another represent hydrogen, methyl,    ethyl, trifluoromethyl, difluoromethyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or    methoxy;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F),        (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H),        (CF₃,F).

In a further embodiment (Embodiment 4-3), the particularly preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen, methyl, ethyl, methoxy, cyclopropyl or    trifluoromethyl;-   R³ and R⁶ independently of one another represent    difluorochloromethyl, cyclopropyl or phenyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or    methoxy;-   X represents hydrogen, chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F),        (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H),        (CF₃,F).

In a further embodiment (Embodiment 4-4), the particularly preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen, methyl, ethyl, methoxy, cyclopropyl or    trifluoromethyl;-   R³ and R⁶ independently of one another represent hydrogen, fluorine,    methyl, ethyl, isopropyl, trifluoromethyl, pentafluoroethyl,    difluoromethyl, 1,1-difluoroethyl, difluorochloromethyl, cyclopropyl    or phenyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or    methoxy;-   X represents hydrogen, chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F),        (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H),        (CF₃,F).

In a further embodiment (Embodiment 4-5), the particularly preferredsubstituents or ranges of the radicals given in the compounds of theformula (I) are as follows:

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen, methyl, ethyl, methoxy, cyclopropyl or    trifluoromethyl;-   R³ and R⁶ independently of one another represent fluorine,    isopropyl, pentafluoroethyl, 1,1-difluoroethyl,    difluorochloromethyl, cyclopropyl or phenyl;-   W represents hydrogen or fluorine;-   n represents the number 0 or 1;-   Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or    methoxy;-   X represents hydrogen, chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F),        (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H),        (CF₃,F).

Very particularly preferred substituents or ranges for the radicalsshown in the compounds of the formula (I) are illustrated below(Embodiment 5-1).

-   V represents oxygen;-   Q represents C—R⁵, where-   R⁵ represents hydrogen;-   R³ represents trifluoromethyl;-   R⁶ represents hydrogen;-   represents fluorine;-   n represents the number 0 or 1;-   Y represents chlorine or methyl;-   X represents chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,F), (Me,Me), (Cl,Cl).

In a further embodiment (Embodiment 5-2), the very particularlypreferred substituents or ranges of the radicals given in the compoundsof the formula (I) are as follows:

-   V represents oxygen;-   represents C—R⁵, where-   R⁵ represents hydrogen or methyl;-   R³ represents hydrogen, methyl, ethyl, cyclopropyl, isopropyl,    difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl    or phenyl;-   R⁶ represents hydrogen, fluorine or methyl;-   W represents fluorine;-   n represents the number 0 or 1;-   Y represents bromine, chlorine or methyl;-   X represents hydrogen, chlorine, fluorine or methyl;    -   where X and Y represent in particular the following combinations        (Y,X): (Me,H), (Me,Cl), (Me,F), (Me,Me), (Cl,Cl), (Cl,F),        (Cl,H), (Br,F).

When sulphur and/or nitrogen occur in rings in the above definitions,for example in expressions such as “in which the rings may contain atleast one heteroatom from the group of sulphur, oxygen (where oxygenatoms must not be directly adjacent) and nitrogen” or “in which one ortwo ring members may each be replaced by a heteroatom from the group ofsulphur, oxygen (where oxygen atoms must not be directly adjacent) andnitrogen”, unless stated otherwise, the sulphur may also be present inthe form of SO or SO₂; the nitrogen, if it is not in the form of —N═, aswell as NH, may also be in the form of N-alkyl (especiallyN—C₁-C₆-alkyl).

In the broadest and the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl,1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl,1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl,1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl,benzoisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl,indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl,benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl,isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl.

In the further preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated up to the maximum possible number of substituents. Inthe case of polyhalogenation, the halogen atoms can be identical ordifferent. Halogen is fluorine, chlorine, bromine and iodine, especiallyfluorine, chlorine and bromine.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,may each be straight-chain or branched if possible, including incombination with heteroatoms, as, for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted, wherethe substituents in the case of polysubstitution may be the same ordifferent. If substituents are intended or optionally intended, thesubstitutents are, unless indicated otherwise, halogen, alkyl,cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particularfluorine, chlorine, (C₁-C₃)-alkyl, (C₃-C₆)-cycloalkyl (in particularcyclopropyl), cyano, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or(C₁-C₃)-haloalkoxy.

The radical definitions or elucidations given above in general terms orwithin preferred ranges apply correspondingly to the end products(including the compounds of the formula (I) with the substructure (I-A),which will be elucidated later), and to the starting materials andintermediates. These radical definitions can be combined with oneanother as desired, i.e. including combinations between the respectivepreferred ranges.

Preference is given in accordance with the invention to compounds of theformula (I) in which a combination of the definitions given above aspreferred is present, and every embodiment described above as preferredconstitutes an independent combination, in particular a combination asdescribed in Embodiment 2-1 or in Embodiment 2-2 or in Embodiment 2-3.

More preference is given in accordance with the invention to compoundsof the formula (I) in which a combination of the definitions given aboveas more preferred is present, and every embodiment described above asmore preferred constitutes an independent combination, in particular acombination as described in Embodiment 3-1 or in Embodiment 3-2 or inEmbodiment 3-3.

Particular preference is given in accordance with the invention tocompounds of the formula (I) in which a combination of the definitionsgiven above as particularly preferred is present, and every embodimentdescribed above as particularly preferred constitutes an independentcombination, in particular a combination as described in Embodiment 4-1or in Embodiment 4-2 or in Embodiment 4-3 or in Embodiment 4-4 or inEmbodiment 4-5.

Very particular preference is given in accordance with the invention tocompounds of the formula (I) in which a combination of the definitionsgiven above as very particularly preferred is present, and everyembodiment described above as very particularly preferred constitutes anindependent combination, in particular a combination as described inEmbodiment 5-1 or in Embodiment 5-2.

In further preferred embodiments, the invention relates to compounds ofthe formula (I) in which Q represents C—R⁵. This results in compounds ofthe formula (I-A)

In the compounds of the formula (I) defined by the structure (I-A), theradicals or structural elements R⁵, R³, R⁶, W, n, Y and X have themeanings described above, in particular as described in Embodiment 1-1.

More particularly, X and Y represent the following (Y,X) combinations:(Me,F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F), (MeO,F), (MeO,H),(Cl,H), (Br,H), (Br,F), (F,F), (CF₃,H), (CF₃,F), particular preferencebeing given to the following (Y,X) combinations: (Me,F), (Me,Me),(Cl,Cl).

Preferred from among the compounds of the formula (I) defined bystructure (I-A) are those compounds in which a combination of themeanings given above as preferred is present, and every embodimentdescribed above as preferred constitutes an independent combination, inparticular a combination as described in Embodiment 2-1 or in Embodiment2-2 or in Embodiment 2-3.

More preferred from among the compounds of the formula (I) defined bystructure (I-A) are those compounds in which a combination of themeanings given above as more preferred is present, and every embodimentdescribed above as more preferred constitutes an independentcombination, in particular a combination as described in Embodiment 3-1or in Embodiment 3-2 or in Embodiment 3-3.

Particularly preferred from among the compounds of the formula (I)defined by structure (I-A) are those compounds in which a combination ofthe meanings given above as particularly preferred is present, and everyembodiment described above as particularly preferred constitutes anindependent combination, in particular a combination as described inEmbodiment 4-1 or in Embodiment 4-2 or in Embodiment 4-3 or inEmbodiment 4-4 or in Embodiment 4-5.

Very particularly preferred from among the compounds of the formula (I)defined by structure (I-A) are those compounds in which a combination ofthe meanings given above as very particularly preferred is present, andevery embodiment described above as very particularly preferredconstitutes an independent combination, in particular a combination asdescribed in Embodiment 5-1 or in Embodiment 5-2.

The compounds of the formula (I) can also be present as salts, inparticular acid addition salts and metal salt complexes. The compoundsof the formula (I) and the acid addition salts and metal salt complexesthereof have good efficacy, especially for controlling animal pests,which include arthropods and in particular insects and acarids.

Suitable salts of the compounds of the general formula (I) includecustomary nontoxic salts, i.e. salts with appropriate bases and saltswith added acids. Preference is given to salts with inorganic bases,such as alkali metal salts, for example sodium, potassium or caesiumsalts, alkaline earth metal salts, for example calcium or magnesiumsalts, ammonium salts, salts with organic bases and with inorganicamines, for example triethylammonium, dicyclohexylammonium,N,N′-dibenzylethylenediammonium, pyridinium, picolinium orethanolammonium salts, salts with inorganic acids, for examplehydrochlorides, hydrobromides, dihydrosulphates, trihydrosulphates, orphosphates, salts with organic carboxylic acids or sulphonic acids, forexample formates, acetates, trifluoroacetates, maleates, tartrates,methanesulphonates, benzenesulphonates or para-toluenesulphonates, saltswith basic amino acids, for example arginates, aspartates or glutamates,and the like.

The compounds of the formula (I) may possibly also, depending on thenature of the substituents, be in the form of stereoisomers, i.e. in theform of geometric and/or optically active isomers or isomer mixtures ofvarying composition. This invention provides both the pure stereoisomersand any desired mixtures of these isomers, even though it is generallyonly compounds of the formula (I) that are discussed here.

However, preference is given in accordance with the invention to usingthe optically active, stereoisomeric forms of the compounds of theformula (I) and salts thereof.

The invention therefore relates both to the pure enantiomers anddiastereomers and to mixtures thereof for controlling animal pests,including arthropods and especially insects and acarids. An individualconfiguration of the invention is therefore directed to the presence ofthe R enantiomer, or to a mixture comprising a majority of the Renantiomer, preferably where the ratio of R to S enantiomer is at least60:40 and, with increasing preference, at least 70:30, 75:25, 80:20,85:15 and 90:10. A further individual configuration of the invention istherefore directed to the presence of the S enantiomer, or to a mixturecomprising a majority of the S enantiomer, preferably where the ratio ofS to R enantiomer is at least 60:40 and, with increasing preference, atleast 70:30, 75:25, 80:20, 85:15 and 90:10.

The compounds of the formula (I) may be present in different polymorphicforms or as a mixture of different polymorphic forms. Both the purepolymorphs and the polymorph mixtures form part of the subject-matter ofthe invention and can be used in accordance with the invention.

The compounds according to the invention are defined in general terms bythe formula (I), which includes all the possible rotamers and mixturesthereof.

The compounds of the formula (I) according to the invention can beprepared by customary methods known to those skilled in the art. Variouspreparation processes, which also form part of the subject-matter of theinvention, are described below.

Preparation Processes

The compounds of the general formula (I) can be classified intocompounds where n=0 (Ia), n=1 (Ib) and n=2 (Ic) and can be preparedaccording to the scheme below, for example according to Methods A and B,as described in the application WO 2010/100189. In deviation from thesemethods, the compounds of the formula (I) can also be prepared byProcesses D and E or the Processes F and G illustrated below, or byprocesses described in WO1999/055668.

Process A

Compounds of the formula (Ma) or tautomers thereof can be prepared, forexample, according to Process A by reacting anilines of the formula(IVa) with nitro compounds of the formula (V) in which R* representshydroxy or halogen (preferably Cl and Br).

Many different methods for preparing carboxamides from carboxylic acids(R*=hydroxy) or carbonyl halides (R=halogen) are known, for example G.Benz in Comprehensive Organic Synthesis, 1^(st) Ed., Pergamon Press,Oxford, 1991, Vol. 6, pp. 381-417; P. D. Bailey et al. in ComprehensiveOrganic Functional Group Transformation, 1st Ed., Elsevier Science Ltd.,Oxford, 1995, Vol. 5, pp. 257-308 and R. C. Larock in ComprehensiveOrganic Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999,pp. 1929-1994. Carbonyl chlorides can be isolated or used as generatedin situ.

The amidation reactions are optionally carried out in the presence of acondensing agent, optionally in the presence of an acid activator,optionally in the presence of an acid acceptor and optionally in thepresence of a solvent. Useful condensing agents are all the condensingagents typically usable for such amidation reactions. Examples which maybe mentioned are acid halide formers such as phosgene, phosphorustrichloride, oxalyl chloride or thionyl chloride; carbodiimides such asN,N′-dicyclohexylcarbodiimide (DCC) and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI), or other customarycondensing agents such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-chloropyridine 1-methoiodide (Mukaiyama'sreagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/carbon tetrachloride, bromotripyrrolidinophosphoniumhexafluorophosphate (BROP),O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphoniumhexafluorophosphate (BOP), N,N,N′,N′-bis(tetramethylene)chlorouroniumtetrafluoroborate, O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HBTU),O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uroniumhexafluorophosphate,O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(TBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uroniumtetrafluoroborate,O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) and 1-hydroxybenzotriazole. These reagentscan be used separately or, if appropriate, in combination. Useful acidacceptors are all customary inorganic or organic bases, for exampletriethylamine, diisopropylethylamine, N-methylmorpholine orN,N-dimethylaminopyridine. Process A according to the invention isoptionally carried out in the presence of a suitable reaction auxiliary,for example N,N-dimethylformamide or N,N-dimethylaminopyridine.

Furthermore, it is also possible to use mixed anhydrides for preparing(Ma), as published, for example, in J. Am. Chem. Soc 1967, 5012. In thisprocess, it is possible to use various chloroformic esters, for exampleisobutyl chloroformate, isopropyl chloroformate. It is likewise possiblefor this purpose to use diethylacetyl chloride, trimethylacetyl chlorideand the like.

Compounds of the general formula (IIa) or tautomers thereof can beprepared, for example, by reduction of the nitro compounds of thegeneral formula (Ma) according to methods known from the literature.Suitable processes for such reductions are in particular metal-mediatedreactions such as, for example, tin(II) chloride, iron powder, zincpowder, Raney nickel, palladium(0) on carbon or platinum dioxide (ashydrate). The metal-mediated reductions, for example with tin(II)chloride, can be carried out according to a process described in OrganicSyntheses Coll. Vol. (III), 453.

Process B

Alternatively, compounds of the general formula (IIa) can be prepared byan acylation reaction according to Process B where an aniline of thegeneral formula (IVa) is reacted with a suitable carboxylic acidderivative of the formula (VI), where R** preferably represents alkyl.This can take place without activation, as described by B. M. Trost andI. Fleming in Comprehensive Organic Synthesis, Ed. Pergamon, 1991, Vol.6. Alternatively, the literature discloses activation methods byformation of an aluminium amide, as by T. Ooi and K. Marouka in Scienceof Synthesis, Ed. Georg Thieme, 2003, Vol. 7, 225-246. These aluminiumamides can be obtained from the anilines or their salts by reaction withtrimethylaluminium or their air-stable adduct with1,4-diazobicyclo[2.2.3]octane (DABCO), as described by S. Woodward inTet. Lett. 2006, 47, 5767-5769.

R** may also represent hydrogen, so that all synthesis methods describedin Process A would also be suitable for the synthesis of compounds ofthe formula (IIa).

Various methods are suitable for the preparation of thioethers of thegeneral formula (Ia). Examples which may be mentioned are: starting withcompounds of the formula (IIa) by ring closure; starting with anilinesof the formula (IVa) by reaction with compounds of the formula (IX)according to Process C or starting with halides of the formula (VIIa) orboronic acids of the formula (VIIIa) or (VIIIb) by metal-catalysedreactions according to Process D or Process E.

Cyclization

For Q=C—R⁵, where R⁵ represents H or alkyl, the preparation of thethioether of the general formula (Ia) can take place according tomethods known from the literature by cyclization of open-chainprecursors of the formula (IIa) with an orthoester such as triethylorthoformate or triethyl orthoacetate, optionally in the presence of asolvent and diluent, optionally in the presence of an acid of organicnature (such as para-toluenesulphonic acid) or inorganic nature (such ashydrochloric acid or sulphuric acid) in catalytic or stoichiometricamounts or in excess or instead of the solvent or diluent.Alternatively, the thioether of the general formula (Ia) can be preparedby methods known from the literature by reaction with DMF-DMA andsubsequent reaction with formic acid.

For Q=C—R⁵, where R⁵ represents alkyl or haloalkyl, the preparation ofthe thioether of the general formula (Ia) can also be carried out byreaction with the appropriate carboxylic anhydrides or acid chloridesaccording to methods known from the literature, for example as describedfor R⁵═CF₃ in the patent WO 2008/039489.

For Q=N, the compounds of the formula (Ia) can be prepared bydiazotization of the compounds of the formula (IIa) according to methodsknown from the literature. For example, a nitrite source such as sodiumnitrite or isobutyl nitrite is added to compounds of the formula (IIa),typically in water, alcohol or a polar inert solvent, at from 0 to 5° C.in the presence of an organic or inorganic acid. Exemplary reactionconditions can be found, for example, in the patent WO 2004/242572 or inJ. Amer. Chem. Soc. Perkin Trans. 1, 1980, 633-638.

Process C

Alternatively, the compounds of the formula (Ia) can be prepared fromanilines of the formula (IVa) by reaction with compounds of the formula(IX) or their tautomeric hydroxypyrimidinones according to Process C. Asdescribed by Yang et al. in Org. Lett. 2009, 11, 6, 1421-1424, theN-arylation of the hydroxypyrimidinones is carried out under mildreaction conditions, for example by HATU-mediated coupling with primaryamines using DBU as base in acetonitrile as solvent, in most cases atroom temperature or at up to 70° C.

Process D

An alternative preparation of the compounds of the formula (Ia) isprovided by the reaction of halides of the formula (VIIa) with compoundsof the formula (IX) under metal-catalysed reaction conditions. Theliterature discloses numerous methods, for example in Chem. Pharm. Bull.1997, 45, 4, 719-721; in Tet. Lett. 2006, 47, 7677-7680; or Synlett2008, 9, 1335-1340, where the metal source used is copper iodide in thepresence of a base and optionally a ligand at elevated temperatures (forexample from 120 to 150° C.).

Process E

It has likewise been found that the reaction of boronic acids of theformula (VIIIa) with compounds of the formula (IX) by metal-catalysedreactions may serve to prepare the compounds of the formula (Ia). Anoverview of such reactions can be found in Synthesis 2011, 6, 829-856. Asuitable metal source is copper(II) acetate, as in Synlett 2010, 5,721-724; Tetrahedron 2006, 62, 8, 1764-1771; Tetrahedron Lett. 2005, 46,34, 5699-5702 or WO 2010/104818.

The oxidation of the boronic acids of the formula (VIIIa) or theirboronic esters according to methods known from the literature, forexample with sodium periodate, leads to sulphoxides of the formula(VIIIb) which can likewise be reacted with compounds of the formula (IX)under metal-catalysed reaction conditions, resulting in the targetcompounds (Ib).

When carrying out the Processes D and E according to the invention, anycommercial microwave apparatus suitable for these reactions mayoptionally be employed (for example Anton Paar Monowave 300, CEMDiscover S, Biotage Initiator 60).

Alternatively, compounds of the general formula (Ib) may be prepared bymethods similar to those mentioned here carried out in a differentorder, for example by oxidation of the anilines of the formula (IVa) togive sulphoxides of the formula (IVb) and their further conversionaccording to Process A, B or C.

In deviation from these methods, the compounds of the formula (I) whereQ=C—R⁵ can also be prepared according to Process F.

Anilines of the formula (IVa) can be reacted with oxazinones of theformula (XXII) to give target compounds of the formula (Ia), for exampleaccording to Assiut Univ. J. of Chemistry 2006, 45-63. Oxazinones of theformula (XXII) are known or can be prepared by methods known from theliterature, for example as in Journal of the Chemical Society 1965,4240-4246.

In deviation from these methods, the compounds of the formula (I) canalso be prepared according to Process G.

Anilines of the formula (IVa) can be reacted with β-keto esters of theformula (XXX) to give enols of the formula (XXXI), for example accordingto WO 2004/056785. The amination of the enols of the formula (XXXI) withan aminating agent such as ammoniak or ammonium acetate affords theopen-chain compound of the formula (IIa). The preparation of thecompounds of the formula (I) from (IIa) has already been describedabove.

Reactions in the Microwave

In the performance of the processes according to the invention, it isoptionally possible to use any commercial microwave apparatus suitablefor these reactions (e.g. Anton Paar Monowave 300, CEM Discover S,Biotage Initiator 60).

Thionation

A further general process for preparing the compounds of the generalformula (Ia) or (Ib) according to the invention in which V is sulphurinvolves the conversion of the carbonyl in corresponding precursors tothe thiocarbonyl group with the aid of suitable thionating reagents, forexample phosphorus pentasulphide or Lawesson's reagent in a suitablesolvent, for example pyridine, xylene or cumene. This variant isdescribed in numerous publications, for example in J. Amer. Chem. Soc.1956, 1938-1941, Chem. Pharm. Bull. 1962, 10, 647-652, U.S. Pat. No.3,007,927, DE 2554866 or WO 2000026194.

General Preparation Processes for Oxidizing Thioethers to Sulphoxides

Compounds of the general formula (Ib) can be prepared through oxidationby processes known from the literature from compounds of the generalformula (Ia), for example by means of an oxidizing agent in a suitablesolvent and diluent. Suitable oxidizing agents are, for example, dilutenitric acid, hydrogen peroxide and peroxycarboxylic acids, for examplemeta-chloroperbenzoic acid. Suitable solvents are inert organicsolvents, typically acetonitrile and halogenated solvents such asdichloromethane, chloroform or dichloroethane.

A large number of different methods are suitable for generatingenantiomerically enriched sulphoxides, as described by A. R. Maguire inARKIVOC, 2011(i), 1-110: metal-catalysed asymmetric oxidations ofthioethers, for example with titanium or vanadium as the most frequentlyemployed catalyst sources, in the form of Ti(O^(i)Pr₄) or VO(acac)₂,together with a chiral ligand and an oxidizing agent such as tert-butylhydroperoxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP) orhydrogen peroxide; non-metal-catalysed asymmetric oxidations employingchiral oxidizing agents or chiral catalysts; electrochemical orbiological asymmetric oxidations and also kinetic resolution ofsulphoxides and nucleophilic shift (according to Andersen's method).

The enantiomers can also be obtained from the racemate, for example byseparating them on a preparative scale by chiral HPLC.

Description of the Starting Materials and Intermediates

Anilines of the formula (IV), halides of the formula (VII) and boronicacids of the formula (VIII) are central building blocks for preparingthe compounds of the formula (I).

The anilines of the general formula (IV) can be classified intocompounds where n=0 (IVa) and n=1 (IVb).

Anilines of the formula (IVa) are known from the literature, for examplefrom JP 2007/284356, or they can be synthesized by processes known fromthe literature.

The anilines of the general formula (IVa) can be prepared, for example,as in the scheme below;

where X, Y and W have the meanings given above, AG represents a leavinggroup and PG represents a protecting group.

Anilines of the formula (XIV) are either commercially available or canbe prepared by known methods. They can be protected with a suitableprotective group, for example an acetyl group, to give compounds of theformula (XIII). In the presence of acids, acid anhydrides or acidchlorides, for example, the anilines (XIV) can be converted to thecorresponding anilides (XIII). The chlorosulphonation of the protectedanilines (XIII) with chlorosulphonic acid gives the correspondingsulphonyl chlorides (XII). The reduction of the sulphonyl chlorides(XII) to the disulphides (XI) is possible by methods known from theliterature, for example iron in hydrochloric acid or iodide. Thereaction of the disulphides (XI) with haloalkyl electrophiles of theformula (XV) where AG is a leaving group, for example chlorine, bromine,tosylate, mesylate or triflate, gives the sulphides (X). The protectinggroup can be removed by suitable methods known from the literature, soas to obtain anilines of the formula (IVa).

Instead of the reduction to the disulphide (XI), the sulphonyl chloride(XII) can be reduced with a suitable reducing agent, for exampleiodine/phosphorus, to give the alkyl thioate (XVII), and thendeprotected by a suitable method, for example the reaction withpotassium hydroxide solution, to give thiols of the formula (XVI).Reaction of the thiols (XVI) with haloalkyl electrophiles of the formula(XV) where AG represents a leaving group such as, for example, chlorine,bromine, tosylate, mesylate or triflate affords the sulphides (IVa).

Likewise preferably, the thioethers of the formula (IVa) canalternatively be prepared according to the following scheme:

where X, Y and W have the meanings given above, AG represents a leavinggroup and PG represents a protecting group.

The chlorosulphonation of the nitroaromatics of the formula (XXI) withchlorosulphonic acid gives the corresponding sulphonyl chlorides (XX).The reduction of the sulphonyl chlorides (XX) to the bis(nitroaryl)disulphides (XIX) is possible by methods known from the literature, forexample iodide. The reduction of the disulphides (XIX) to thedisulphanediyldianilines (XVIII), some of which are formed as a mixturewith the corresponding aminoarylthiols (XVI), is possible with commonlyknown reducing agents, for example hydrogen, optionally with the aid ofheterogeneous catalysts, for example, Raney nickel, platinum onactivated carbon or palladium on activated carbon. Reaction of thedisulphides (XVIII) or thiophenols (XVI) with haloalkyl electrophiles ofthe formula (XV) where AG represents a leaving group such as, forexample, chlorine, bromine, iodine, tosylate, mesylate or triflateaffords the 3-[(2,2,2-trifluoroethyl)sulphanyl]anilines of the formula(IVa).

Halides of the General Formula (VIIa)

in which X, Y and W have the meanings given above and Hal representschlorine, bromine or iodine are known from the literature, from WO2007/034755, JP 2007/081019, JP 2007/284385, JP 2008/260706, JP2008/308448, JP 2009/023910 or WO 2012/176856, or can be synthesized byprocesses known from the literature, which may optionally be slightlymodified.

Suitable starting materials for the synthesis of the iodides of thegeneral formula (VIIa) are bromides having the same formula, for examplein halogen exchange reactions according to methods known from theliterature, if appropriate with metal catalysis (see H. Suzuki, Chem.Let. 1985, 3, 411-412; S. L. Buchwald, J. Amer. Chem. Soc. 2002, 124(50), 14844-14845). Synthesis is likewise possible proceeding fromanilines of the formula (IVa) under Sandmeyer reaction conditions, asdescribed by E. B. Merkushev in Synthesis 1988, 12, 923-937.

Boronic Acids of the General Formula (VIIIa) and (VIIIb)

in which X, Y and W have the meanings given above are known from theliterature, for example from WO2007/034755, JP2007/284385, JP2009/023910and WO2012/176856, or can be synthesized by processes known from theliterature.

Of particular interest are furthermore intermediates shown in theprocesses and methods described. These intermediates also form part ofthe subject matter of the invention. In addition to the intermediatesdescribed above, further intermediates are described below.

The Invention Furthermore Provides a Compound of the Formula (IIa)

in which R³, R⁶, W, X and Y have the meanings given above.

Preferred compounds of the formula (IIa) are those in which acombination of the definitions given above as preferred is present, andevery embodiment described above as preferred constitutes an independentcombination.

More preferred compounds of the formula (IIa) are those in which acombination of the definitions given above as more preferred is present,and every embodiment described above as more preferred constitutes anindependent combination.

Particularly preferred compounds of the formula (IIa) are those in whicha combination of the definitions given above as particularly preferredis present, and every embodiment described above as particularlypreferred constitutes an independent combination.

Very particularly preferred compounds of the formula (IIa) are those inwhich a combination of the definitions given above as very particularlypreferred is present, and every embodiment described above as veryparticularly preferred constitutes an independent combination.

The compounds of the formula (IIa) can be present in differenttautomeric forms. These forms are therefore also embraced, even if notexplicitly shown.

The Invention Furthermore Provides a Compound of the Formula (XXXI)

in which R³, R⁶, W, X and Y have the meanings given above.

Preferred compounds of the formula (XXXI) are those in which acombination of the definitions given above as preferred is present, andevery configuration described above as preferred constitutes anindependent combination.

More preferred compounds of the formula (XXXI) are those in which acombination of the definitions given above as more preferred is present,and every embodiment described above as more preferred constitutes anindependent combination.

Particularly preferred compounds of the formula (XXXI) are those inwhich a combination of the definitions given above as particularlypreferred is present, and every embodiment described above asparticularly preferred constitutes an independent combination.

Very particularly preferred compounds of the formula (XXXI) are those inwhich a combination of the definitions given above as very particularlypreferred is present, and every embodiment described above as veryparticularly preferred constitutes an independent combination.

The compounds of the formula (XXXI) can be present in differenttautomeric forms. These forms are therefore also embraced, even if notexplicitly shown.

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. Accordingly, the inventionencompasses both pure stereoisomers and any mixtures of these isomers.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection.Preferably excluded from this are methods for the surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticide” alsoalways comprises the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in horticulture, in animal husbandry, in aquatic cultures,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector. They canpreferably be used as pesticides. They are effective against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coniferarum, Oligonychusilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychuspratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp.,Ornithonyssus spp., Panonychus spp., for example Panonychus citri(=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., for example Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., for example Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;from the class of the Diplopoda, for example Blaniulus guttulatus;from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp.,Periplaneta spp., for example Periplaneta americana, Periplanetaaustralasiae, Supella longipalpa;from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,for example Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., for example Anthonomus grandis, Anthrenus spp., Apionspp., Apogonia spp., Atomaria spp., for example Atomaria linearis,Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.,for example Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotomatrifurcata, Ceutorrhynchus spp., for example Ceutorrhynchus assimilis,Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., forexample Chaetocnema confinis, Chaetocnema denticulata, Chaetocnemaectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., for exampleCosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculiospp., for example Curculio caryae, Curculio caryatrypes, Curculioobtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus,Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturusspp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestesspp., Diabrotica spp., for example Diabrotica balteata, Diabroticabarberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctataundecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgiferazeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp.,Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp.,Melanotus spp., for example Melanotus longulus oregonensis, Meligethesaeneus, Melolontha spp., for example Melolontha melolontha, Migdolusspp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagusoryzae, Otiorhynchus spp., for example Otiorhynchus cribricollis,Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchusrugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedoncochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.,for example Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotretaramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.,Prostephanus truncatus, Psylliodes spp., for example Psylliodes affinis,Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobiusventralis, Rhizopertha dominica, Sitophilus spp., for example Sitophilusgranarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais,Sphenophorus spp., Stegobium paniceum, Sternechus spp., for exampleSternechus paludatus, Symphyletes spp., Tanymecus spp., for exampleTanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebriomolitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fanniaspp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrelliaspp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp.,Liriomyza spp., for example Liriomyza brassicae, Liriomyza huidobrensis,Liriomyza sativae, Lucilia spp., for example Lucilia cuprina, Lutzomyiaspp., Mansonia spp., Musca spp., for example Musca domestica, Muscadomestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,Paralauterborniella subcincta, Pegomya spp., for example Pegomya betae,Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp.,Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletisspp., for example Rhagoletis cingulata, Rhagoletis completa, Rhagoletisfausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex;from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis,Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., forexample Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., for example Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., for example Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., for example Aspidiotus nerii, Atanus spp., Aulacorthumsolani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspismelaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicorynebrassicae, Cacopsylla spp., for example Cacopsylla pyricola, Calligyponamarginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,for example Coccus hesperidum, Coccus longulus, Coccuspseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp.,Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri,Diaspis spp., Drosicha spp., Dysaphis spp., for example Dysaphisapiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp.,Empoasca spp., for example Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for exampleEriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana,Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis,Hyalopterus pruni, Icerya spp., for example Icerya purchasi, Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., forexample Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., forexample Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula,Macrosiphum spp., for example Macrosiphum euphorbiae, Macrosiphum lilii,Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphissacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,Monellia costalis, Monelliopsis pecanis, Myzus spp., for example Myzusascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzuspersicae, Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., forexample Nephotettix cincticeps, Nephotettix nigropictus, Nilaparvatalugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis,Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for exampleParatrioza cockerelli, Parlatoria spp., Pemphigus spp., for examplePemphigus bursarius, Pemphigus populivenae, Peregrinus maidis,Phenacoccus spp., for example Phenacoccus madeirensis, Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., for example Phylloxeradevastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcusspp., for example Planococcus citri, Prosopidopsylla flava,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., for example Pseudococcus calceolariae, Pseudococcus comstocki,Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni,Psyllopsis spp., Psylla spp., for example Psylla buxi, Psylla mali,Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., forexample Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., for example Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., for example Saissetia coffeae, Saissetia miranda, Saissetianeglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum,Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., for example Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., for example Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;from the suborder of the Heteroptera, for example Anasa tristis,Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylommalivida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimexhemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., for example Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horciasnobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossusoccidentalis, Leptoglossus phyllopus, Lygocoris spp., for exampleLygocoris pabulinus, Lygus spp., for example Lygus elisus, Lygushesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum,Nezara spp., for example Nezara viridula, Oebalus spp., Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Diprion spp., for exampleDiprion similis, Hoplocampa spp., for example Hoplocampa cookei,Hoplocampa testudinea, Lasius spp., Monomorium pharaonis, Sirex spp.,Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., forexample Vespa crabro, Xeris spp.;from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;from the order of the Isoptera, for example Coptotermes spp., forexample Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermesspp., for example Reticulitermes flavipes, Reticulitermes hesperus;from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrixthurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.,Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposinaniponensis, Cheimatobia brumata, Chilo spp., for example Chiloplejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium,Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for exampleEphestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctisspp., for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp.,Galleria mellonella, Gracillaria spp., Grapholitha spp., for exampleGrapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpaspp., for example Helicoverpa armigera, Helicoverpa zea, Heliothis spp.,for example Heliothis virescens, Hofmannophila pseudospretella,Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoriaflavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., forexample Leucoptera coffeella, Lithocolletis spp., for exampleLithocolletis blancardella, Lithophane antennata, Lobesia spp., forexample Lobesia botrana, Loxagrotis albicosta, Lymantria spp., forexample Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitisleda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogoncloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp.,Ostrinia spp., for example Ostrinia nubilalis, Oulema melanopus, Oulemaoryzae, Panolis flammea, Parnara spp., Pectinophora spp., for examplePectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., forexample Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., for example Phyllonorycter blancardella, Phyllonoryctercrataegella, Pieris spp., for example Pieris rapae, Platynota stultana,Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., for example Pseudaletia unipuncta, Pseudoplusia includens,Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., for exampleSchoenobius bipunctifer, Scirpophaga spp., for example Scirpophagainnotata, Scotia segetum, Sesamia spp., for example Sesamia inferens,Sparganothis spp., Spodoptera spp., for example Spodoptera eradiana,Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Teciasolanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella,Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusiaspp., for example Trichoplusia ni, Tryporyza incertulas, Tuta absoluta,Virachola spp.;from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;from the order of the Siphonaptera, for example, Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens,Frankliniella spp., for example Frankliniella fusca, Frankliniellaoccidentalis, Frankliniella schultzei, Frankliniella tritici,Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp.,Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp.,Taeniothrips cardamomi, Thrips spp., for example Thrips palmi, Thripstabaci;from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;pests from the phylum of the Mollusca, for example from the class of theBivalvia, for example Dreissena spp.,and also from the class of the Gastropoda, for example Anion spp., forexample Anion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;animal and human parasites from the phyla of the Platyhelminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephalaspp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp.,Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp.,Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp.,Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilariaspp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobiusspp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsisspp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronemaspp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepisspp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylusspp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muelleriusspp., Necator spp., Nematodirus spp., Nippostrongylus spp.,Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp.,Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp.,Parafilaria spp., Paragonimus spp., Paramphistomum spp.,Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylusspp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilariaspp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamusspp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp.,Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylusspp., Trichuris spp., Uncinaria spp., Wuchereria spp.;plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, especially Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorusspp., for example Longidorus africanus, Meloidogyne spp., for exampleMeloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp.,Paraphelenchus spp., Paratrichodorus spp., for example Paratrichodorusminor, Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

In addition, it is possible to control, from the sub-kingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

Nematodes

In the present context, the term “nematodes” comprises all species ofthe phylum Nematoda and here in particular species acting as parasiteson plants or fungi (for example species of the order Aphelenchida,Meloidogyne, Tylenchida and others) or else on humans and animals (forexample species of the orders Trichinellida, Tylenchida, Rhabditida andSpirurida) and causing damage in or on these living organisms, and alsoother parasitic helminths.

A nematicide in crop protection, as described herein, is capable ofcontrolling nematodes.

The term “controlling nematodes” means killing the nematodes orpreventing or impeding their development or their growth or preventingor impeding their penetration into or their sucking on plant tissue.

Here, the efficacy of the compounds is determined by comparingmortalities, gall formation, cyst formation, nematode density per volumeof soil, nematode density per root, number of nematode eggs per soilvolume, mobility of the nematodes between a plant or plant part treatedwith the compound of the formula (I) or the treated soil and anuntreated plant or plant part or the untreated soil (100%). Preferably,the reduction achieved is 25-50% in comparison to an untreated plant,plant part or the untreated soil, particularly preferably 51-79% andvery particularly preferably the complete kill or the completeprevention of development and growth of the nematodes by a reduction of80 to 100%. The control of nematodes as described herein also comprisesthe control of proliferation of the nematodes (development of cystsand/or eggs). Compounds of the formula (I) can also be used to keep theplants or animals healthy, and they can be employed curatively,preventatively or systemically for the control of nematodes.

The person skilled in the art knows methods for determining mortalities,gall formation, cyst formation, nematode density per volume of soil,nematode density per root, number of nematode eggs per volume of soil,mobility of the nematodes.

The use of a compound of the formula (I) may keep the plant healthy andalso comprises a reduction of the damage caused by nematodes and anincrease of the harvest yield.

In the present context, the term “nematodes” refers to plant nematodeswhich comprise all nematodes which damage plants. Plant nematodescomprise phytoparasitic nematodes and soil-borne nematodes. Thephytoparasitic nematodes include ectoparasites such as Xiphinema spp.,Longidorus spp. and Trichodorus spp.; semiparasites such as Tylenchulusspp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp.and Scutellonema spp.; non-migratory parasites such as Heterodera spp.,Globodera spp. and Meloidogyne spp., and also stem and leafendoparasites such as Ditylenchus spp., Aphelenchoides spp. andHirschmaniella spp. Particularly damaging root-parasitic soil nematodesare, for example, cyst-forming nematodes of the genera Heterodera orGlobodera, and/or root gall nematodes of the genus Meloidogyne. Damagingspecies of these genera are, for example, Meloidogyne incognita,Heterodera glycines (soya bean cyst nematode), Globodera pallida andGlobodera rostochiensis (yellow potato cyst nematode), these speciesbeing controlled effectively by the compounds described in the presenttext. However, the use of the compounds described in the present text isby no means restricted to these genera or species, but also extends inthe same manner to other nematodes.

The plant nematodes include, for example, Aglenchus agricola, Anguinatritici, Aphelenchoides arachidis, Aphelenchoides fragaria, and the stemand leaf endoparasites Aphelenchoides spp., Belonolaimus gracilis,Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus andBursaphelenchus spp., Cacopaurus pestis, Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp.,Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum andCriconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci,Ditylenchus myceliophagus and also the stem and leaf endoparasitesDitylenchus spp., Dolichodorus heterocephalus, Globodera pallida(=Heterodera pallida), Globodera rostochiensis (yellow potato cystnematode), Globodera solanacearum, Globodera tabacum, Globodera virginiaand the non-migratory cyst-forming parasites Globodera spp.,Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchuserythrine, Helicotylenchus multicinctus, Helicotylenchus nannus,Helicotylenchus pseudorobustus and Helicotylenchus spp.,Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata,Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae,Heterodera glycines (soya bean cyst nematode), Heterodera oryzae,Heterodera schachtii, Heterodera zeae and the non-migratory cyst-formingparasites Heterodera spp., Hirschmaniella gracilis, Hirschmaniellaoryzae, Hirschmaniella spinicaudata and the stem and leaf endoparasitesHirschmaniella spp., Hoplolaimus aegyptii, Hoplolaimus californicus,Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus,Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus,Longidorus breviannulatus, Longidorus elongatus, Longidoruslaevicapitatus, Longidorus vineacola and the ectoparasites Longidorusspp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria,Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogynechitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyneexigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogynegraminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyneincognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis,Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis,Meloidogyne thamesi and the non-migratory parasites Meloidogyne spp.,Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchuspseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus,Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus,Paratrichodorus teres and Paratrichodorus spp., Paratylenchus hamatus,Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp.,Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus,Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae,Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchusgiibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchushexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchuspenetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchusteres, Pratylenchus thomei, Pratylenchus vulnus, Pratylenchus zeae andthe migratory endoparasites Pratylenchus spp., Pseudohalenchus minutus,Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis,Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, themigratory endoparasites Radopholus spp., Rotylenchulus borealis,Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp.,Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus,Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyurum,Scutellonema bradys, Scutellonema clathricaudatum and the migratoryendoparasites Scutellonema spp., Subanguina radiciola, Tetylenchusnicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorusprimitivus, Trichodorus proximus, Trichodorus similis, Trichodorussparsus and the ectoparasites Trichodorus spp., Tylenchorhynchus agri,Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchusclaytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis,Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchusvulgaris and Tylenchorhynchus spp., Tylenchulus semipenetrans and thesemiparasites Tylenchulus spp., Xiphinema americanum, Xiphinemabrevicolle, Xiphinema dimorphicaudatum, Xiphinema index and theectoparasites Xiphinema spp.

Nematodes for the control of which a compound of the formula (I) may beused include nematodes of the genus Meloidogyne such as the Southernroot-knot nematode (Meloidogyne incognita), the Javanese root-knotnematode (Meloidogyne javanica), the Northern root-knot nematode(Meloidogyne hapla) and the peanut root-knot nematode (Meloidogynearenaria); nematodes of the genus Ditylenchus such as the potato rotnematode (Ditylenchus destructor) and stem and bulb eelworm (Ditylenchusdipsaci); nematodes of the genus Pratylenchus such as the cobroot-lesion nematode (Pratylenchus penetrans), the chrysanthemumroot-lesion nematode (Pratylenchus fallax), the coffee root nematode(Pratylenchus coffeae), the tea root nematode (Pratylenchus loosi) andthe walnut root-lesion nematode (Pratylenchus vulnus); nematodes of thegenus Globodera such as the yellow potato cyst nematode (Globoderarostochiensis) and the white potato cyst nematode (Globodera pallida);nematodes of the genus Heterodera such as the soya bean cyst nematode(Heterodera glycines) and beet cyst eelworm (Heterodera schachtii);nematodes of the genus Aphelenchoides such as the rice white-tipnematode (Aphelenchoides besseyi), the chrysanthemum nematode(Aphelenchoides ritzemabosi) and the strawberry nematode (Aphelenchoidesfragariae); nematodes of the genus Aphelenchus such as the fungivorousnematode (Aphelenchus avenae); nematodes of the genus Radopholus, suchas the burrowing nematode (Radopholus similis); nematodes of the genusTylenchulus such as the citrus root nematode (Tylenchulussemipenetrans); nematodes of the genus Rotylenchulus such as thereniform nematode (Rotylenchulus reniformis); tree-dwelling nematodessuch as the pine wood nematode (Bursaphelenchus xylophilus) and the redring nematode (Bursaphelenchus cocophilus) and the like.

Plants for the protection of which a compound of the formula (I) can beused include plants such as cereals (for example rice, barley, wheat,rye, oats, maize and the like), beans (soya bean, aduki bean, bean,broadbean, peas, peanuts and the like), fruit trees/fruits (apples,citrus species, pears, grapevines, peaches, Japanese apricots, cherries,walnuts, almonds, bananas, strawberries and the like), vegetable species(cabbage, tomato, spinach, broccoli, lettuce, onions, spring onion,pepper and the like), root crops (carrot, potato, sweet potato, radish,lotus root, turnip and the like), plant for industrial raw materials(cotton, hemp, paper mulberry, mitsumata, rape, beet, hops, sugar cane,sugar beet, olive, rubber, palm trees, coffee, tobacco, tea and thelike), cucurbits (pumpkin, cucumber, watermelon, melon and the like),meadow plants (cocksfoot, sorghum, timothy-grass, clover, alfalfa andthe like), lawn grasses (mascarene grass, bentgrass and the like), spiceplants etc. (lavender, rosemary, thyme, parsley, pepper, ginger and thelike) and flowers (chrysanthemums, rose, orchid and the like).

The compounds of the formula (I) are particularly suitable forcontrolling coffee nematodes, in particular Pratylenchus brachyurus,Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita,Meloidogyne coffeicola, Helicotylenchus spp. and also Meloidogyneparanaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. andScutellonema spp.

The compounds of the formula (I) are particularly suitable forcontrolling potato nematodes, in particular Pratylenchus brachyurus,Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans,Pratylenchus coffeae, Ditylenchus dipsaci and of Pratylenchus alleni,Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus,Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus,Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus,Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorusprimitivus, Trichodorus proximus, Trichodorus similis, Trichodorussparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorusnanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita,Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans,Globodera rostochiensis, Globodera pallida, Ditylenchus destructor,Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi,Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinemaspp.

The compounds of the formula (I) are particularly suitable forcontrolling tomato nematodes, in particular Meloidogyne arenaria,Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita,Pratylenchus penetrans and also Pratylenchus brachyurus, Pratylenchuscoffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorusminor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum,Dolichodorus heterocephalus and Rotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling cucumber plant nematodes, in particular Meloidogynearenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyneincognita, Rotylenchulus reniformis and Pratylenchus thornei.

The compounds of the formula (I) are particularly suitable forcontrolling cotton nematodes, in particular Belonolaimus longicaudatus,Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus andRotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling maize nematodes, in particular Belonolaimus longicaudatus,Paratrichodorus minor and also Pratylenchus brachyurus, Pratylenchusdelattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchuszeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorusbreviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi,Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognitaacrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae,Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchusdipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimusgaleatus, Hoplolaimus indicus, Helicotylenchus digonicus,Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinemaamericanum, Dolichodorus heterocephalus, Criconemella ornata,Criconemella onoensis, Radopholus similis, Rotylenchulus borealis,Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus,Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchusnudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchusminutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici,Aphelenchoides arachidis, Scutellonema brachyurum and Subanguinaradiciola.

The compounds of the formula (I) are particularly suitable forcontrolling soya bean nematodes, in particular Pratylenchus brachyurus,Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri,Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbusand also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchusneglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchusagilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis),Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica,Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus andRotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling tobacco nematodes, in particular Meloidogyne incognita,Meloidogyne javanica and also Pratylenchus brachyurus, Pratylenchuspratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchusneglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchusvulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus,Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globoderatabacum, Globodera solanacearum, Globodera virginiae, Ditylenchusdipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum,Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni,Paratylenchus spp. and Tetylenchus nicotianae.

The compounds of the formula (I) are particularly suitable forcontrolling citrus nematodes, in particular Pratylenchus coffeae andalso Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimuslongicaudatus, Paratrichodorus minor, Paratrichodorus porosus,Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita,Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum,Xiphinema brevicolle, Xiphinema index, Criconemella spp.,Hemicriconemoides, Radopholus similis and Radopholus citrophilus,Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulussemipenetrans.

The compounds of the formula (I) are particularly suitable forcontrolling banana nematodes, in particular Pratylenchus coffeae,Radopholus similis and also Pratylenchus giibbicaudatus, Pratylenchusloosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchusdihystera and Rotylenchulus spp.

The compounds of the formula (I) are particularly suitable forcontrolling pineapple nematodes, in particular Pratylenchus zeae,Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi.,Meloidogyne spp., Rotylenchulus reniformis and also Longidoruselongatus, Longidorus laevicapitatus, Trichodorus primitivus,Trichodorus minor, Heterodera spp., Ditylenchus myceliophagus,Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus,Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchusmulticinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum,Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchusebriensis, Paratylenchus minutus, Scutellonema clathricaudatum,Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens,Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoenseand Criconemoides ornatum.

The compounds of the formula (I) are particularly suitable forcontrolling grapevine nematodes, in particular Pratylenchus vulnus,Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica,Xiphinema americanum, Xiphinema index and also Pratylenchus pratensis,Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus,Pratylenchus thornei and Tylenchulus semipenetrans.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops—pome fruit, in particularPratylenchus penetrans and also Pratylenchus vulnus, Longidoruselongatus, Meloidogyne incognita and Meloidogyne hapla.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops—stone fruit, in particularPratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria,Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita,Criconemella xenoplax and of Pratylenchus brachyurus, Pratylenchuscoffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimuslongicaudatus, Helicotylenchus dihystera, Xiphinema americanum,Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus,Paratylenchus projectus, Scutellonema brachyurum and Hoplolaimusgaleatus.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops, sugar cane and rice, in particularTrichodorus spp., Criconemella spp. and also Pratylenchus spp.,Paratrichodorus spp., Meloidogyne spp., Helicotylenchus spp.,Tylenchorhynchus spp., Aphelenchoides spp., Heterodera spp, Xiphinemaspp. and Cacopaurus pestis.

In the present context, the term “nematodes” also refers to nematodesdamaging humans or animals.

Specific nematode species harmful to humans or to animals are:

Trichinellida, for example: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.;

From the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.

From the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;From the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;

Many known nematicides also act against other parasitic helminths andare therefore used for controlling worms—not necessarily belonging tothe group Nematoda—which are parasites in humans and animals. Thepresent invention also relates to the use of the compounds of theformula (I) as anthelmintic medicaments. The pathogenic endoparasitichelminths include Platyhelminthes (e.g. Monogenea, cestodes andtrematodes), Acanthocephala and Pentastoma. The following helminths maybe mentioned as being preferred:

Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.

Cestodes: from the order of the Pseudophyllidea, for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diplogonoporus spp.

From the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diochis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.

Trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp., Metorchis spp., Heterophyes spp., Metagonimus spp.

Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example: Moniliformis spp.

From the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the administration ofthe compounds of the formula (I) is carried out by methods generallyknown in the art, directly or enterally, parenterally, dermally ornasally in the form of suitable preparations. Administration may beprophylactic or therapeutic.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropyl guar polymers and/orhumectants, for example glycerol and/or fertilizers, for exampleammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

These are preferably formulations or use forms which compriseauxiliaries, for example extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or further auxiliaries, for example adjuvants. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having anybiological effect. Examples of adjuvants are agents which promoteretention, spreading, attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are produced either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, such as cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, such asmethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, such as dimethylsulphoxide, and also water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as finely divided silica, alumina and natural orsynthetic silicates, resins, waxes and/or solid fertilizers. Mixtures ofsuch carriers can likewise be used. Useful carriers for granulesinclude: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite, dolomite, and synthetic granules ofinorganic and organic meals, and also granules of organic material suchas sawdust, paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Particularlysuitable extenders or carriers are those which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellant gases, such as halohydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents with ionic or nonionic properties, or mixtures of thesesurfactants, include salts of polyacrylic acid, salts of lignosulphonicacid, salts of phenolsulphonic acid or naphthalenesulphonic acid,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulphosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulphates, sulphonates andphosphates, for example alkylaryl polyglycol ethers, alkyl sulphonates,alkylsulphates, arylsulphonates, protein hydrolyzates, lignosulphitewaste liquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and when the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove chemical and/or physical stability. Foam generators or antifoamsmay also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders,granules or latices, such as gum arabic, polyvinyl alcohol and polyvinylacetate, or else natural phospholipids such as cephalins and lecithinsand synthetic phospholipids. Further possible auxiliaries are mineraland vegetable oils.

Optionally, further auxiliaries may be present in the formulations andthe use forms derived therefrom. Examples of such additives includefragrances, protective colloids, binders, adhesives, thickeners,thixotropic agents, penetrants, retention promoters, stabilizers,sequestrants, complexing agents, humectants, spreaders. In general, thecompounds of the formula (I) can be combined with any solid or liquidadditive commonly used for formulation purposes.

Useful retention promoters include all those substances which reduce thedynamic surface tension, for example dioctyl sulphosuccinate, orincrease the viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the (generally aqueous) applicationliquor and/or from the spray coating into the cuticle of the plant andthereby increase the mobility of active compounds in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001 and 98% byweight of the compound of the formula (I), with particular preference,between 0.01% and 95% by weight of the compound of the formula (I), morepreferably between 0.5% and 90% by weight of the compound of the formula(I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) may also be employed as a mixture withone or more suitable fungicides, bactericides, acaricides,molluscicides, nematicides, insecticides, microbiologicals, beneficialspecies, herbicides, fertilizers, bird repellents, phytotonics,sterilants, safeners, semiochemicals and/or plant growth regulators, inorder thus, for example, to broaden the spectrum of action, to prolongthe duration of action, to increase the rate of action, to preventrepulsion or prevent evolution of resistance. In addition, activecompound combinations of this kind can improve plant growth and/ortolerance to abiotic factors, for example high or low temperatures, todrought or to elevated water content or soil salinity. It is alsopossible to improve flowering and fruiting performance, optimizegermination capacity and root development, facilitate harvesting andimprove yields, influence maturation, improve the quality and/or thenutritional value of the harvested products, prolong storage life and/orimprove the processability of the harvested products.

Furthermore, the compounds of the formula (I) can be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellants and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used in mixtures with agents to improve plant properties, forexample growth, yield and quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case.

Insecticides/Acaricides/Nematicides:

The active compounds identified here by their common names are known andare described, for example, in the pesticide handbook (“The PesticideManual” 16th Ed., British Crop Protection Council 2012) or can be foundon the Internet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulphan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos,chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon,dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulphoton,EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,fosthiazate, heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulphotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.(2) GABA-gated chloride channel antagonists, for examplecyclodiene-organochlorines, e.g. chlordane and endosulphan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.(3) Sodium channel modulators/voltage-gated sodium channel blockers, forexample pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrins-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin,empenthrin [(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox,imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer],prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen,tefluthrin, tetramethrin, tetramethrin [(1R) isomer)], tralomethrin andtransfluthrin or DDT or methoxychlor.(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for exampleneonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulphoxaflor.(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR), for example spinosyns, e.g. spinetoram and spinosad.(6) Chloride channel activators, for example, avermectins/milbemycins,e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.(7) Juvenile hormone imitators, for example, juvenile hormone analoguese.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.(8) Active compounds with unknown or nonspecific mechanisms of action,for example alkyl halides, e.g. methyl bromide and other alkyl halides;or chloropicrine or sulphuryl fluoride or borax or tartar emetic.(9) Selective antifeedants, e.g. pymetrozine or flonicamid.(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox anddiflovidazin or etoxazole.(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus sphaericus, Bacillusthuringiensis subspecies aizawai, Bacillus thuringiensis subspecieskurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plantproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab1.(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin andfenbutatin oxide or propargite or tetradifon.(13) Oxidative phosphorylation decouplers that interrupt the H protongradient, for example chlorfenapyr, DNOC and sulphluramid.(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.(15) Chitin biosynthesis inhibitors, type 0, for example bistrifluron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron andtriflumuron.(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.(17) Moulting inhibitors (in particular for Diptera, i.e. dipterans)such as, for example, cyromazine.(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.(19) Octopaminergic agonists, for example amitraz.(20) Complex-III electron transport inhibitors, for examplehydramethylnon; or acequinocyl; or fluacrypyrim.(21) Complex-I electron transport inhibitors, for example from the groupof the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.(24) Complex-IV electron transport inhibitors, for example phosphines,e.g. aluminium phosphide, calcium phosphide, phosphine and zincphosphide or cyanide.(25) Complex-II electron transport inhibitors, for example cyenopyrafenand cyflumetofen.(28) Ryanodine receptor effectors, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,further active compounds, for example afidopyropen, azadirachtin,benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat,cryolite,dicofol, diflovidazin, fluensulphone, flometoquin, flufenerim,flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide,heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding,pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin andiodomethane; and also preparations based on Bacillus firmus (1-1582,BioNeem, Votivo), and also the following compounds:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) and1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (knownfrom WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate(known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO2005/085216),4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide(known from WO2009/002809), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]phthalamide(known from WO2012/034472),8-chloro-N-[(2-chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide(known from WO2010/129500),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929), (5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine(known from WO2010/069266),(2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide(known from WO2010/060231),4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969).Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” or on the Internet (forexample; http://www.alanwood.net/pesticides).

(1) Ergosterol biosynthesis inhibitors, for example (1.1) aldimorph,(1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5)cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8)diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorphacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol,(1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18)fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21)flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,(1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64)O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate,(1.65) pyrisoxazole.(2) Respiration inhibitors (respiratory chain inhibitors), for example(2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5)fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9)furametpyr, (2.10) furmecyclox, (2.11) isopyrazam mixture of thesyn-epimeric racemate 1RS,4SR,9RS and the anti-empimeric racemate1RS,4SR,9SR, (2.12) isopyrazam (anti-epimeric racemate), (2.13)isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxane, (2.23) thifluzamide, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine,(2.29) benzovindiflupyr, (2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideand (2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid(3) Respiration inhibitors (respiratory chain inhibitors) that act oncomplex III of the respiratory chain, for example (3.1) ametoctradin,(3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5)coumethoxystrobin, (3.6) coumoxystrobin, (3.5) dimoxystrobin, (3.8)enestroburin, (3.9) famoxadone, (3.10) fenamidone, (3.11)flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14)metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17)pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20)pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.28)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(3.29)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.30) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxypheny)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,(3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(4) inhibitors of mitosis and cell division, for example (4.1) benomyl,(4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5)ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8) pencycuron,(4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate,(4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine and (4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.(5) Compounds having multisite activity such as, for example, (5.1)Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil,(5.5) copper preparations such as copper hydroxide, (5.6) coppernaphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) coppersulphate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13)dodine free base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) folpet,(5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20)iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22)mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zincmetiram, (5.27) copper-oxine, (5.28) propamidine, (5.29) propineb,(5.30) sulphur and sulphur preparations such as, for example calciumpolysulphide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34)ziram and (5.35) anilazine.(6) Resistance inducers, for example (6.1) acibenzolar-S-methyl, (6.2)isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin(7) Amino acid and protein biosynthesis inhibitors, for example (7.1)andoprim, (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin,(7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7)pyrimethanil, (7.8)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolineand (7.9) oxytetracycline and (7.10) streptomycin.(8) ATP production inhibitors, for example (8.1) fentin acetate, (8.2)fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.(9) Cell wall synthesis inhibitors, for example (9.1) benthiavalicarb,(9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5)mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A,(9.9) valifenalate and (9.10) polyoxin B.(10) Lipid and membrane synthesis inhibitors, for example (10.1)biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos, (10.5)etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane,(10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11)prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazeneand (10.15) tolclofos-methyl.(11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid,(11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon,(11.6) tricyclazole and (11.7) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.(12) Nucleic acid synthesis inhibitors, for example (12.1) benalaxyl,(12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon,(12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8)hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14)octhilinone.(13) Signal transduction inhibitors, for example (13.1) chlozolinate,(13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5)procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8)proquinazid.(14) Decouplers, for example (14.1) binapacryl, (14.2) dinocap, (14.3)ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.(15) Further compounds such as, for example, (15.1) benthiazole, (15.2)bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat,(15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid,(15.9) cymoxanil, (15.10) cyprosulphamide, (15.11) dazomet, (15.12)debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15)difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine,(15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21)fluorimid, (15.22) flusulphamide, (15.23) flutianil, (15.24)fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium,(15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulphocarb,(15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin,(15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35)nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38)oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40)phenothrin, (15.41) phosphoric acid and its salts, (15.42)propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph,(15.45)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.46)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50)tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid,(15.54) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (15.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl1H-imidazole-1-carboxylate, (15.59)2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.60)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.64)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.67) 2-phenylphenol and salts, (15.68)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.85)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93)quinolin-8-ol sulphate (2:1), (15.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.95)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.96)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.97)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.98)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.99)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(15.100)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.101)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.102) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.103)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.104)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.105)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.106)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.107) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (15.108)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.109)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(15.110)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.111)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.112)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.113)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.114)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.120) propyl3,4,5-trihydroxybenzoate, (15.121)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(15.122)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.123)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.124)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.129)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.132)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.133)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.134)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.135)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.136)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.137)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.138)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.139)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.140)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.141)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.143)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.144)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.148)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.149) abscisic acid, (15.150)3-(difluoromethyl)-N-methoxy-1-methyl-N41-(2,4,6-trichlorophenyl)propan-2-yl-1H-pyrazole-4-carboxamide,(15.151)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.152)N′-{5-bromo-6-[1-(3,5-difluoropheny)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.153)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.154)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.155)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.156)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.158)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.159)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.160)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.161)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.162)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.163)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.164)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.165)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.166)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.167)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.168)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.169)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.170)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.171)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.172)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.173)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.174)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.175)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.176)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamide,(15.177)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.178)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.179)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.180)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.181)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.All the mixing partners mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups.Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides include especially bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which can be used as biological pesticidesare:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, inparticular strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, in particular strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, inparticular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Acession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39. (AccessionNumber CNCM 1-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suilins spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners such as,for example, benoxacor, cloquintocet (-mexyl), cyometrinil,cyprosulphamide, dichlormid, fenchlorazole (-ethyl), fenclorim,flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and parts of plants can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, peas and other vegetable species, cotton,tobacco, oilseed rape, and also fruit plants (with the fruits apples,pears, citrus fruits and grapevines). Crop plants may be plants whichcan be obtained by conventional breeding and optimization methods or bybiotechnological and genetic engineering methods or combinations ofthese methods, including the transgenic plants and including the plantcultivars which are protectable and non-protectable by plant breeders'rights. Parts of plants shall be understood to mean all parts and organsof the plants above and below ground, such as shoot, leaf, flower androot, examples given being leaves, needles, stalks, stems, flowers,fruit bodies, fruits and seeds, and also tubers, roots and rhizomes.Parts of plants also include harvested material and vegetative andgenerative propagation material, for example cuttings, tubers, rhizomes,slips and seeds.

Treatment according to the invention of the plants and plant parts withthe compounds of the formula (I) is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering methods, ifappropriate in combination with conventional methods (geneticallymodified organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above. Particularpreference is given in accordance with the invention to treating plantsof the respective commercially customary cultivars or those that are inuse. Plant cultivars are understood to mean plants having new properties(“traits”) and which have been obtained by conventional breeding, bymutagenesis or by recombinant DNA techniques. They may be cultivars,varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefultraits to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to levels of water or soil salinity, enhancedflowering performance, easier harvesting, accelerated ripening, higheryields, higher quality and/or higher nutritional value of the harvestedproducts, better storage life and/or processibility of the harvestedproducts. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as against insects, arachnids, nematodes, mites,slugs and snails owing, for example, to toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF andalso combinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinothricin (for example the “PAT”gene). The genes which impart the desired traits in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants include the important crop plants, such ascereals (wheat, rice, triticale, barley, rye, oats), maize, soya beans,potatoes, sugar beet, sugar cane, tomatoes, peas and other types ofvegetable, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), particular emphasisbeing given to maize, soya beans, wheat, rice, potatoes, cotton, sugarcane, tobacco and oilseed rape. Traits which are particularly emphasizedare the increased resistance of the plants to insects, arachnids,nematodes and slugs and snails.

Crop Protection—Types of Treatment

The treatment of the plants and plant parts with the compounds of theformula (I) is carried out directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, furthermore as a powder fordry seed treatment, a solution for liquid seed treatment, awater-soluble powder for slurry treatment, by incrusting, by coatingwith one or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.the compounds of the formula (I) are applied to the foliage, wheretreatment frequency and the application rate should be adjustedaccording to the level of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I) areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also beaccomplished by metering the compound of the formula (I) in a solidapplication form (for example as granules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvement. However, thetreatment of seed entails a series of problems which cannot always besolved in a satisfactory manner Thus, it is desirable to develop methodsfor protecting the seed and the germinating plant which dispense with,or at least reduce considerably, the additional application ofpesticides during storage, after sowing or after emergence of theplants. It is additionally desirable to optimize the amount of activecompound used so as to provide optimum protection for the seed and thegerminating plant from attack by animal pests, but without damage to theplant itself by the active compound used. In particular, methods for thetreatment of seed should also take account of the intrinsic insecticidalor nematicidal properties of pest-resistant or -tolerant transgenicplants in order to achieve optimal protection of the seed and thegerminating plant with a minimum expenditure of crop protectionproducts.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It also comprises amethod where the seed is treated at different times with a compound ofthe formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) for protection from animal pests. Theinvention also relates to seed which has been treated simultaneouslywith a compound of the formula (I) and a mixing component. The inventionfurther relates to seed which has been treated at different times with acompound of the formula (I) and a mixing component. In the case of seedwhich has been treated at different times with a compound of the formula(I) and a mixing component, the individual substances may be present onthe seed in different layers. In this case, the layers comprising acompound of the formula (I) and mixing components may optionally beseparated by an intermediate layer. The invention also relates to seedin which a compound of the formula (I) and a mixing component have beenapplied as part of a coating or as a further layer or further layers inaddition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions or compounds of signalling technology, leading tobetter colonization by symbionts such as, for example, rhizobia,mycorrhizae and/or endophytic bacteria or fungi, and/or to optimizednitrogen fixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this includes seed ofcereals (for example wheat, barley, rye, millet and oats), corn, cotton,soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola, oilseedrape, beets (for example sugarbeets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya, cotton,canola, oilseed rape and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for the treatment of transgenic seed containing atleast one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed ina suitable formulation. Suitable formulations and processes for seedtreatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customary seeddressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives such as, forexample, customary extenders and also solvents or diluents, colorants,wetting agents, dispersants, emulsifiers, antifoams, preservatives,secondary thickeners, adhesives, gibberellins and also water.

Dyes which may be present in the seed dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of active agrochemical compounds. Preference is given tousing alkyl naphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical compounds. Preference is given tousing nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristryrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants areespecially lignosulphonates, polyacrylic acid salts andarylsulphonate/formaldehyde condensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalcompounds. Silicone antifoams and magnesium stearate can be used withpreference.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful adhesives which may be present in the seed dressing formulationsusable in accordance with the invention are all customary binders usablein seed dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom byadding water, all mixing units usable customarily for the seed dressingare useful. Specifically, the procedure in seed dressing is to place theseed into a mixer in batchwise or continuous operation, to add theparticular desired amount of seed dressing formulations, either as suchor after prior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. in the field of veterinary medicine,the compounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasites”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects and acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable homeotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer,and particularly cattle and pigs; poultry such as turkeys, ducks, geese,and particularly chickens; fish and crustaceans, for example inaquaculture, and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,cage birds, reptiles, amphibians and aquarium fish.

In a preferred embodiment, the compounds of the formula (I) areadministered to mammals.

In another preferred embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds and particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the animal health field, the term “control” or“controlling” means that the compounds of the formula (I) are effectivein reducing the incidence of the particular parasite in an animalinfected with such parasites to an innocuous degree. More specifically,“controlling” in the present context means that the compound of theformula (I) can kill the respective parasite, inhibit its growth, orinhibit its proliferation.

Arthropods include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; fromthe order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; from the order of the Diptera and thesuborders Nematocerina and Brachycerina, for example Aedes spp.,Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomusspp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp.,Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; from the order of the Siphonapterida, for example Pulexspp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllusspp.;from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.; and also nuisance and hygienepests from the order of the Blattarida.

Arthropods further include:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example from the family of Argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodesspp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the originalgenus of multi-host ticks); from the order of Mesostigmata likeDermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietiaspp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.;from the order of the Actinedida (Prostigmata), for example Acarapisspp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorusspp.; and from the order of the Acaridida (Astigmata), for exampleAcarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp.,Laminosioptes spp.

Parasitic Protozoa include:

Mastigophora (Flagellata), for example Trypanosomatidae, for example,Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense,T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T.vivax, Leishmania brasiliensis, L. donovani, L. tropica, for exampleTrichomonadidae, for example, Giardia lamblia, G. canis;Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp.,Harmanella sp.;Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E.ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example,Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitiabesnoitii; such as Sarcocystidae, for example, Sarcocystis bovicanis, S.bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S.suihominis, such as Leucozoidae, for example, Leucozytozoon simondi,such as Plasmodiidae, for example, Plasmodium berghei, P. falciparum, P.malariae, P. ovale, P. vivax, P. spec., such as Piroplasmea, forexample, Babesia argentina, B. bovis, B. canis, B. spec., Theileriaparva, Theileria spec., such as Adeleina, for example, Hepatozoon canis,H. spec.

Pathogenic endoparasites, which are helminths, include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), roundworms, Acanthocephala,and Pentastoma. These include:

monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.;

cestodes: from the order of the Pseudophyllidea for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diplogonoporus spp.;

from the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diochis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp., Metorchis spp., Heterophyes spp., Metagonimus spp.;roundworms: Trichinellida, for example: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.;from the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.;from the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;from the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example Moniliformis spp.;from the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.;Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic ortherapeutic.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, especially as a helminthicidal agent orantiprotozoic agent, for example in animal husbandry, in animalbreeding, in buildings for live stock and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic, in particular an arthropodicide such as aninsecticide or an acaricide. A further aspect relates to the use of acompound of the formula (I) as an antiectoparasitic, in particular anarthropodicide such as an insecticide or an acaricide, for example inanimal husbandry, in animal breeding, in buildings for live stock or inthe hygiene sector.

Anthelmintic Mixing Components

The following anthelmintic mixing components may be mentioned by way ofexample:

anthelmintically active compounds including trematicidally andcestocidally active compounds:

from the class of the macrocyclic lactones, for example: abamectin,doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin,nemadectin, selamectin;

from the class of the benzimidazoles and probenzimidazoles, for example:albendazole, albendazole-sulphoxide, cambendazole, cyclobendazole,febantel, fenbendazole, flubendazole, mebendazole, netobimin,oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate,triclabendazole;from the class of the cyclooctadepsipeptides, for example: emodepside,PF1022;from the class of the aminoacetonitrile derivatives, for example:monepantel;from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;from the class of the salicylanilides, for example: bromoxanide,brotianide, clioxanide, closantel, niclosamide, oxyclozanide,rafoxanide, tribromsalan;from the class of the paraherquamides, for example: derquantel,paraherquamide;from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;from the class of the organophosphates, for example: coumaphos,crufomate, dichlorvos, haloxone, naphthalofos, trichlorfon;from the class of the substituted phenols, for example: bithionol,disophenol, hexachlorophene, niclofolan, meniclopholan, nitroxynil;from the class of the piperazinones, for example: praziquantel,epsiprantel;from various other classes, for example: amoscanate, bephenium,bunamidine, clonazepam, clorsulon, diamfenetid, dichlorophen,diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, Miracil,mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz,omphalotin, oxamniquin, paromomycin, piperazine, resorantel.Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample, viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host or after injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simuliidae: transmission of worms, in particular Onchocerca        volvulus;        2) Lice: skin infections, epidemic typhus;        3) Fleas: plague, endemic typhus;        4) Flies: sleeping sickness (trypanosomiasis); cholera, other        bacterial diseases;        5) Mites: acariosis, epidemic typhus, rickettsialpox,        tularaemia, Saint Louis encephalitis, tick-borne encephalitis        (TBE), Crimean-Congo haemorrhagic fever, borreliosis;        6) Ticks: borellioses such as Borrelia duttoni, tick-borne        encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia        canis canis).

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, lice, fleas, flies, mites and ticks, whichcan transmit pathogens to animals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, inforestry, in gardens and in leisure facilities, and also in theprotection of materials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. they can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic sector, in the hygiene sector and in the protectionof stored products, particularly for control of insects, arachnids andmites encountered in enclosed spaces, for example dwellings, factoryhalls, offices, vehicle cabins. For controlling animal pests, thecompounds of the formula (I) are used alone or in combination with otheractive compounds and/or auxiliaries. They are preferably used indomestic insecticide products. The compounds of the formula (I) areeffective against sensitive and resistant species, and against alldevelopmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or in bait stations.

EXAMPLES Elucidation of the Processes and Intermediates

The preparation and use examples which follow illustrate the inventionwithout limiting it. The products were characterized by means of 1H NMRspectroscopy and/or LC-MS (liquid chromatography-mass spectrometry)and/or GC-MS (gas chromatography-mass spectrometry).

The log P values were determined analogously to OECD Guideline 117 (ECDirective 92/69/EEC) by HPLC (high-performance liquid chromatography)using reversed-phase columns (C 18), by the following methods:

[a] The LC-MS determination in the acidic range is effected at pH 2.7with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formicacid) as eluents; linear gradient from 10% acetonitrile to 95%acetonitrile. log P^([b]) is also referred to as log P(HCOOH).[b] LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.log P^([1]) is also referred to as log P(neutral).

Calibration is effected with solutions of a homologous series ofunbranched alkan-2-ones (having 3 to 16 carbon atoms) with known log Pvalues (log P values determined on the basis of the retention times bylinear interpolation between two successive alkanones).

The NMR spectra were measured with a Bruker II Avance 400 equipped witha 1.7 mm TCI probe head. In isolated cases, the NMR spectra weredetermined using a Bruker Avance II 600.

The NMR data for selected examples are listed in conventional form (δvalues, multiplet splitting, number of hydrogen atoms). The splitting ofthe signals was described as follows: s (singlet), d (doublet), t(triplet), q (quartet), m (multiplet), broad (for broad signals).Solvents used were CD₃CN, CDCl₃ or D6-DMSO, and tetramethylsilane (0.00ppm) was used as reference.

The GC-MS spectra are determined using an Agilent 6890 GC, HP 5973 MSDon a dimethylsilicone phase, using a temperature gradient from 50° C. to320° C. GC-MS indices are determined as Kovats indices using solutionsof a homologous series of n-alkanes (having an even number of 8 to 38carbon atoms).

Preparation Example 1:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-6-(trifluoromethyl)pyrimidin-4(3H)-one(Ex. No. 2) Step 1:4,4,4-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-3-hydroxybut-2-enamide(Ex. No. XXXI-1)

2 g (8.36 mmol) of2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline wereinitially charged in 42 ml of toluene. 2.48 ml (16.7 mmol) of ethyl4,4,4-trifluoroacetoacetate and 20.4 mg (0.16 mmol) of 4-DMAP were addedand the reaction mixture was heated under reflux for 14 h. After coolingof the reaction mixture, the solvent was removed under reduced pressureon a rotary evaporator and the residue (3.45 g) was converted into Step2 without further purification.

log P(HCOOH): 2.77

Step 2:3-Amino-4,4,4-trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}but-2-enamide(Ex. No. IIa-1)

The residue (3.45 g) was taken up in ethyl acetate (37.5 ml), andammonium acetate (4.51 g, 58.5 mmol) was added. The reaction mixture washeated under reflux for 7 h. After cooling of the reaction mixture,ethyl acetate (64 ml) was added and the organic phase was washed firstwith water and then with saturated NaCl solution. The organic phase wasdried with MgSO₄ and the solvent was removed under reduced pressure on arotary evaporator. The residue (2.78 g) was converted without furtherpurification into Step 3.

log P(HCOOH): 3.61

Step 3:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-6-(trifluoromethyl)pyrimidin-4(3H)-one(Ex. No. 1)

The residue (2.78 g) was taken up in DMF-DMA (6.2 g) and stirred at 100°C. for 7 h. After cooling of the reaction mixture, the solvent wasremoved under reduced pressure on a rotary evaporator and the residuewas taken up in formic acid (17 ml). The reaction mixture was heatedunder reflux for 2 h. After cooling of the reaction mixture, the solventwas removed under reduced pressure on a rotary evaporator and ethylacetate was added to the residue. The organic phase was washed withwater and dried with MgSO₄. The solvent was removed under reducedpressure on a rotary evaporator and the residue was purified by MPLC(cyclohexane/acetone). This gave 670 mg of the title compound (27% oftheory over the 3 steps, purity 80% according to LC-MS). Furtherpurification by MPLC (cyclohexane/ethyl acetate) gave 157 mg of thetitle compound of a better purity (100% according to LC-MS).

¹H-NMR (D6-DMSO) δ ppm: 8.72 (s, 1H), 7.89 (d, 1H), 7.48 (d, 1H), 7.17(s, 1H), 4.01 (q, 2H), 2.44 (s, 3H)

log P(HCOOH): 3.42 log P(neutral): 3.4

Step 4:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-6-(trifluoromethyl)pyrimidin-4(3H)-one(Ex. No. 2)

190 mg (0.492 mmol) of3-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-6-(trifluoromethyl)pyrimidin-4(3H)-onewere initially charged in methylene chloride, 124 mg (0.541 mmol) ofmeta-chloroperbenzoic acid were added and the reaction mixture wasstirred at 0° C. for 3 h and then extracted with sodium thiosulphate andsodium bicarbonate solution. The organic phase was dried over magnesiumsulphate and filtered. Removal of the solvent under reduced pressuregave 170 mg of the title compound (84% of theory, purity 97% accordingto LC/MS).

¹H-NMR (D6-DMSO) δ ppm: 8.75 (s, 1H), 8.17 (d, 1H), 7.59 (d, 1H), 7.17(s, 1H), 4.29-4.22 (m, 1H), 4.07-4.01 (m, 1H), 2.48 (s, 3H)

log P(HCOOH): 2.4 log P(neutral): 2.38

Preparation Example 2:3-[2,4-Dimethyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-6-(trifluoromethyl)pyrimidin-4-one(Ex. No. 6) Step 1:N-[2,4-Dimethyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-4,4,4-trifluoro-3-hydroxybut-2-enamide(Ex. No. XXXI-2)

5 g (21.2 mmol) of2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline were initiallycharged in 42 ml of toluene. 6.21 ml (42.5 mmol) of ethyl4,4,4-trifluoroacetoacetate and 51.9 mg (0.42 mmol) of 4-DMAP were addedand the reaction mixture was heated under reflux for 14 h. After coolingof the reaction mixture, the solvent was removed under reduced pressureon a rotary evaporator and the residue (7.93 g) was converted into Step2 without further purification.

log P(HCOOH): 2.87

Step 2:3-Amino-N-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-4,4,4-trilluorobut-2-enamide(Ex.-No. Ha-2)

The residue (7.93 g) was taken up in ethyl acetate (82.8 ml), andammonium acetate (6.68 g, 86.6 mmol) was added. The reaction mixture washeated under reflux for 7 h. After cooling of the reaction mixture, thesolvent was removed under reduced pressure on a rotary evaporator. Theresidue (7.91 g) was converted without further purification into Step 3.

log P(HCOOH): 3.63

Step 3:3-[2,4-Dimethyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-6-(trifluoromethyl)pyrimidin-4-one(Ex. No. 5)

The residue (7.91 g) was taken up in triethyl orthoformate (53 ml), andsulphuric acid (0.33 ml) was added. The mixture was stirred at 140° C.for 3 h. After cooling of the reaction mixture, the solvent was removedunder reduced pressure on a rotary evaporator. Water was added to theresidue and the mixture was extracted with ethyl acetate. The organicphase was dried over Na₂SO₄ and filtered. The solvent was removed underreduced pressure on a rotary evaporator and the residue was purified byMPLC (cyclohexane/acetone). This gave 2.99 g of the title compound (37%of theory over the 3 steps, purity 96% according to LC-MS).

¹H-NMR (D6-DMSO) δ ppm: 8.59 (s, 1H), 7.64 (s, 1H), 7.33 (s, 1H), 7.13(s, 1H), 4.00 (q, 2H), 2.38 (s, 3H), 2.04 (s, 3H)

log P(HCOOH): 3.56 log P(neutral): 3.5

Step 4:3-[2,4-Dimethyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-6-(trifluoromethyl)pyrimidin-4-one(Ex. No. 6)

500 mg (1.30 mmol) of3-[2,4-Dimethyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-6-(trifluoromethyl)-pyrimidin-4-onewere initially charged in methylene chloride (25 ml), 331 mg (1.43 mmol)of meta-chloroperbenzoic acid were added and the reaction mixture wasstirred at 0° C. for 1 h and then washed with sodium thiosulphate andsodium bicarbonate solution. The organic phase was dried over sodiumsulphate and filtered. Removal of the solvent under reduced pressuregave 490 mg of the title compound (92% of theory, purity 98% accordingto LC/MS).

¹H-NMR (D6-DMSO) δ ppm: 8.64-8.62 (m, 1H), 7.92 (s, 1H), 7.47-7.44 (m,1H), 7.13 (s, 1H), 4.30-3.88 (m, 2H), 2.43 (s, 3H), 2.15 (s, 3H)

log P(HCOOH): 2.43 log P(neutral): 2.39

The enantiomers were obtained from the racemate by separating thempreparatively by HPLC on a chiral column (ChiralCel OJ-H, e.g. 5 nm250×4.6 mm) using the mobile phase heptane/methanol/ethanol.

The optical rotations were determined on a Perkin Elmer 341, serialnumber 9123, at a wavelength of 589 nm and a temperature of 20° C.

The specific optical rotations below should be understood as an averagefrom 5 different measurements:

Enantiomer 1 (Ex. No. 56): 89.5 in CHCl₃ (c=0.022)

Enantiomer 2 (Ex. No. 49): −87.8 in CHCl₃ (c=0.019)

By the above-described processes, the following compounds of the formula(I) were prepared.

TABLE 1 Compounds of the formula (I) having the substructure (I-A)

W = F and V = O Compound number n Y X R⁵ R³ R⁶  1 0 CH₃ F H CF₃ H  2 1CH₃ F H CF₃ H  3 0 Cl Cl H CF₃ H  4 1 Cl Cl H CF₃ H  5 0 CH₃ CH₃ H CF₃ H 6 1 CH₃ CH₃ H CF₃ H  7 1 CH₃ F H c-Pr H  8 0 CH₃ F CH₃ CF₃ H  9 0 CH₃ FH CF₂CF₃ H 10 1 CH₃ F H CH₂CH₃ H 11 1 CH₃ F H Phenyl H 12 0 CH₃ H H H F13 0 CH₃ CH₃ H CH₃ CH₃ 14 1 CH₃ CH₃ CH₃ CF₃ H 15 0 Br F H CF₃ H 16 0 ClF H CF₃ H 17 1 CH₃ H H CH₂CH₃ H 18 1 CH₃ F H CF₂CF₃ H 19 1 CH₃ F CH₃ CF₃H 20 0 CH₃ CH₃ H CH₃ H 21 0 CH₃ H H H CH₃ 22 0 CH₃ F H CF₂CH₃ H 23 0 CH₃CH₃ H c-Pr H 24 1 CH₃ CH₃ H CH₂CH₃ H 25 0 CH₃ H H H H 26 1 CH₃ F HCF₂CF₃ H 27 1 CH₃ H H H CH₃ 28 1 CH₃ H H H H 29 1 Cl F H CF₃ H 30 0 CH₃CH₃ CH₃ CF₃ H 31 0 CH₃ F H i-Pr H 32 0 CH₃ F H CF₂H H 33 1 CH₃ CH₃ HCF₂CF₃ H 34 1 Cl H H CF₃ H 35 1 CH₃ CH₃ H c-Pr H 36 0 CH₃ CH₃ H CF₂CF₃ H37 0 CH₃ F H c-Pr H 39 0 CH₃ CH₃ H CH₂CH₃ H 40 1 CH₃ H H H F 41 1 Br F HCF₃ H 43 0 CH₃ H H CH₂CH₃ H 44 0 CH₃ F H CH₃ H 45 1 CH₃ CH₃ H CF₂CF₃ H46 1 CH₃ F H CH₃ H 47 0 CH₃ H H CF₃ H 48 1 CH₃ CH₃ H CH₃ CH₃ 49 1 CH₃CH₃ H CF₃ H 50 1 CH₃ H H CF₃ H 51 0 CH₃ CH₃ H CF₂CH₃ H 52 1 CH₃ F H i-PrH 53 1 CH₃ Cl H CF₃ H 54 0 Cl H H CF₃ H 55 1 CH₃ F H CF₂H H 56 1 CH₃ CH₃H CF₃ H 57 0 CH₃ F H CH₂CH₃ H 58 0 CH₃ F H Ph H 59 0 CH₃ Cl H CF₃ H

Furthermore, the following compounds of the formula (IIa) (cf. Table 2)and of the formula (XXXI) (cf. Table 3) were prepared according to theprocesses described above.

TABLE 2 Compounds of the formula IIa (IIa)

where W = F Compound logP logP number Y X R³ R⁶ (HCOOH) (neutral) IIa-1CH₃ F CF₃ H 3.61 3.60 IIa-2 CH₃ CH₃ CF₃ H 3.63 3.61 IIa-3 Cl Cl CF₃ H4.24 4.13 IIa-4 Cl F CF₃ H 3.83 3.73 IIa-5 Br F CF₃ H 3.88 3.78 IIa-6CH₃ H CF₃ H 3.58 3.49 IIa-7 Cl H CF₃ H 3.66 3.65 IIa-8 CH₃ Cl CF₃ H 4.053.99 IIa-9 CH₃ F CF₂H H 3.23 3.21 IIa-10 CH₃ CH₃ CF₂H H 3.24 3.15 IIa-11CH₃ F CF₂CH₃ H 3.55 3.49 IIa-12 CH₃ CH₃ CF₂CH₃ H 3.52 3.40 IIa-13 CH₃ FCF₂CH₃ H 4.09 3.88 IIa-14 CH₃ CH₃ CF₂CH₃ H 4.10 3.99 n.d. = notdetermined

TABLE 3 Compounds of the formula (XXXI) (XXXI)

where W = F Com- pound logP logP number Y X R³ R⁶ (HCOOH) (neutral)XXXI-1 CH₃ F CF₃ H 2.77 1.43 XXXI-2 CH₃ CH₃ CF₃ H 2.87 n.d. XXXI-3 Cl ClCF₃ H 3.13 n.d. XXXI-4 Cl F CF₃ H 2.86 1.45 XXXI-5 Br F CF₃ H 2.93 n.d.XXXI-6 CH₃ H CF₃ H 2.80 n.d. XXXI-7 Cl H CF₃ H 2.84 n.d. XXXI-8 CH₃ ClCF₃ H 3.01 1.44 XXXI-9 CH₃ F CF₂H H 2.47 n.d. XXXI- CH₃ CH₃ CF₂H H 2.53n.d. 10 XXXI- CH₃ F CF₂CH₃ H 2.72 n.d. 11 XXXI- CH₃ CH₃ CF₂CH₃ H n.d.n.d. 12 XXXI- CH₃ F CF₂CF₃ H n.d. n.d. 13 XXXI- CH₃ CH₃ CF₂CF₃ H n.d.1.63 14 n.d. = not determinedNMR Peak List Method

The 1H NMR data of selected examples are stated in the form of 1H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The δ value—signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁);δ (intensity₂); . . . ;δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of the 1H NMR spectra we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may, but need not, occur in NMR peak lists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional 1H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject-matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of 1H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-D6 and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of 1H NMR peak lists can be found in Research DisclosureDatabase Number 564025.

TABLE 4 NMR data of the compounds according to Table 1: Example 1:¹H-NMR(400.0 MHz, DMSO): δ = 9.238(0.6); 8.720(4.4); 8.292(0.7);8.290(0.7); 7.905(2.9); 7.886(3.0); 7.493(2.4); 7.465(2.4); 7.175(4.8);5.758(0.7); 4.047(1.2); 4.022(4.0); 3.996(4.2); 3.970(1.4); 3.322(24.9);2.670(0.4); 2.524(1.3); 2.519(2.1); 2.510(23.9); 2.506(47.6);2.501(62.4); 2.497(44.8); 2.492(21.0); 2.443(16.0); 2.328(0.4);0.008(0.4); 0.000(10.6) Example 2: ¹H-NMR(400.0 MHz, DMSO): δ =9.238(0.7); 8.753(4.7); 8.291(0.8); 8.185(3.1); 8.167(3.1); 7.609(2.3);7.582(2.2); 7.173(5.1); 5.757(4.4); 4.286(0.4); 4.259(0.5); 4.250(0.6);4.223(0.6); 4.070(0.6); 4.044(0.6); 4.034(0.5); 4.008(0.4); 3.321(27.5);2.745(0.7); 2.675(0.4); 2.670(0.6); 2.666(0.4); 2.524(1.8); 2.510(33.0);2.506(64.8); 2.501(84.2); 2.497(60.6); 2.492(29.0); 2.479(16.0);2.333(0.4); 2.328(0.6); 2.324(0.4); 1.236(0.4); 0.000(0.4) Example 3:¹H-NMR(400.0 MHz, DMSO): δ = 9.237(0.7); 9.172(0.6); 9.155(1.9);9.125(0.8); 8.742(2.3); 8.720(9.5); 8.704(0.6); 8.318(4.6); 8.312(4.3);8.290(1.1); 8.131(2.4); 8.129(2.3); 8.093(13.2); 8.070(16.0);8.006(0.8); 7.988(0.4); 7.850(0.5); 7.840(0.6); 7.764(0.4); 7.620(0.6);7.522(0.3); 7.430(0.4); 7.344(0.6); 7.325(0.5); 7.244(11.7); 7.224(0.5);7.185(0.7); 6.781(0.5); 5.958(0.3); 5.537(0.4); 4.246(0.5); 4.231(1.1);4.220(1.8); 4.206(3.4); 4.195(3.5); 4.181(3.6); 4.170(3.5); 4.156(1.9);4.144(1.3); 4.130(0.8); 3.380(0.4); 3.324(311.3); 2.680(2.8);2.675(5.7); 2.671(7.8); 2.666(5.6); 2.662(2.7); 2.639(0.3); 2.620(0.6);2.606(0.4); 2.600(0.4); 2.541(4.7); 2.524(21.0); 2.511(436.6);2.506(875.2); 2.502(1147.4); 2.497(818.8); 2.493(387.3); 2.408(0.4);2.337(2.6); 2.333(5.5); 2.328(7.5); 2.324(5.4); 1.259(0.4); 1.235(1.3);0.146(4.7); 0.027(0.3); 0.008(37.7); 0.000(1067.8); −0.009(37.2);−0.030(1.3); −0.054(0.6); −0.068(0.5); −0.087(0.4); −0.092(0.4);−0.150(4.9) Example 4: ¹H-NMR(400.0 MHz, DMSO): δ = 19.997(1.1);8.714(1.2); 8.663(1.3); 8.316(4.9); 8.303(3.2); 8.290(2.2); 8.269(2.1);7.224(1.5); 7.210(1.4); 3.323(2222.9); 2.675(11.9); 2.671(16.0);2.666(11.6); 2.541(10.5); 2.524(46.3); 2.510(902.8); 2.506(1775.9);2.501(2306.4); 2.497(1634.6); 2.493(766.6); 2.333(10.8); 2.328(14.7);2.324(10.5); 1.234(2.8); 0.838(0.7); 0.146(15.4); 0.008(154.0);0.000(3106.4); −0.009(92.9); −0.150(13.7) Example 5: ¹H-NMR(400.0 MHz,DMSO): δ = 8.588(4.6); 8.316(0.4); 7.641(5.6); 7.328(4.3); 7.126(5.0);5.756(0.5); 4.031(1.2); 4.005(3.9); 3.979(4.0); 3.953(1.4); 3.321(66.0);2.675(0.9); 2.670(1.3); 2.666(0.9); 2.662(0.5); 2.541(0.9); 2.524(3.2);2.510(68.6); 2.506(139.2); 2.501(183.6); 2.497(131.5); 2.492(62.1);2.380(15.2); 2.337(0.4); 2.333(0.9); 2.328(1.2); 2.324(0.9); 2.319(0.4);2.041(16.0); 0.146(0.8); 0.008(6.8); 0.000(196.8); −0.009(6.8);−0.150(0.8) Example 6: ¹H-NMR(400.0 MHz, DMSO): δ = 20.011(0.5);8.637(1.5); 8.620(2.1); 8.316(4.9); 7.918(3.2); 7.464(1.4); 7.439(2.0);7.131(3.1); 5.756(0.4); 4.300(0.5); 4.271(0.5); 4.263(0.5); 4.235(0.5);4.129(0.8); 4.103(0.7); 4.081(0.8); 4.055(0.7); 4.018(0.5); 3.976(0.5);3.945(0.5); 3.919(0.5); 3.883(0.6); 3.399(1.1); 3.391(1.2);3.323(2085.6); 3.268(0.5); 2.980(0.4); 2.937(0.5); 2.675(12.0);2.671(16.0); 2.666(11.5); 2.541(11.4); 2.524(49.6); 2.510(913.2);2.506(1787.3); 2.502(2314.4); 2.497(1649.1); 2.493(779.4); 2.428(10.1);2.337(5.2); 2.333(10.7); 2.328(14.5); 2.324(10.4); 2.153(7.3);2.145(5.1); 1.235(1.6); 0.146(14.5); 0.116(0.6); 0.077(1.1); 0.069(1.0);0.059(1.1); 0.008(138.4); 0.000(3114.1); −0.009(108.4); −0.056(0.6);−0.150(14.2) Example 7: ¹H-NMR(400.0 MHz, DMSO): δ = 8.372 (5.6); 8.009(3.2); 7.991 (3.2); 7.560 (2.5); 7.533 (2.5); 6.493 (6.1); 6.492 (5.9);5.757 (7.9); 4.255 (0.5); 4.247 (0.4); 4.228 (0.6); 4.219 (0.9); 4.192(0.8); 4.165 (0.3); 4.115 (1.0); 4.106 (0.4); 4.088 (1.1); 4.078 (0.7);4.060 (0.4); 4.051 (0.7); 3.329 (25.0); 2.506 (26.1); 2.502 (33.7);2.497 (24.9); 2.464 (16.0); 2.411 (0.5); 2.329 (0.3); 2.012 (0.3); 1.996(1.0); 1.980 (1.5); 1.964 (1.1); 1.948 (0.4); 1.030 (0.4); 1.007 (10.9);0.993 (5.3); 0.988 (5.4); 0.000 (6.4) Example 8: ¹H-NMR(400.0 MHz,DMSO): δ = 7.895 (2.5); 7.876 (2.5); 7.519 (2.2); 7.492 (2.2); 7.058(4.9); 4.063 (0.4); 4.049 (0.5); 4.037 (0.5); 4.023 (1.7); 3.997 (2.4);3.970 (1.7); 3.957 (0.5); 3.944 (0.5); 3.931 (0.4); 3.333 (20.7); 2.671(0.4); 2.525 (1.1); 2.511 (23.8); 2.507 (47.9); 2.502 (62.7); 2.498(46.0); 2.493 (22.8); 2.444 (14.2); 2.375 (1.0); 2.329 (0.4); 2.212(16.0); 0.146 (0.4); 0.008 (3.0); 0.000 (83.1); −0.009 (3.3); −0.150(0.4) Example 9: ¹H-NMR(400.0 MHz, DMSO): δ = 8.734 (4.9); 7.923 (2.9);7.905 (2.9); 7.495 (2.5); 7.468 (2.5); 7.228 (5.6); 7.226 (5.7); 4.050(1.2); 4.024 (3.9); 3.998 (4.1); 3.973 (1.4); 3.322 (31.9); 2.675 (0.4);2.671 (0.5); 2.666 (0.4); 2.524 (1.3); 2.510 (29.4); 2.506 (59.6); 2.502(79.5); 2.497 (59.1); 2.493 (29.8); 2.445 (16.0); 2.333 (0.4); 2.328(0.5); 2.324 (0.4); 0.008 (0.3); 0.000 (10.2); −0.008 (0.4) Example 10:¹H-NMR(400.0 MHz, DMSO): δ = 8.446 (4.8); 8.413 (0.4); 8.316 (0.9);8.029 (2.8); 8.011 (2.8); 7.569 (2.2); 7.542 (2.2); 6.389 (4.3); 6.387(4.3); 4.260 (0.5); 4.251 (0.3); 4.233 (0.6); 4.224 (0.8); 4.196 (0.8);4.128 (0.9); 4.101 (1.0); 4.091 (0.7); 4.074 (0.4); 4.064 (0.6); 3.322(149.5); 2.730 (1.1); 2.675 (1.4); 2.671 (1.9); 2.666 (1.4); 2.586(1.3); 2.567 (3.8); 2.548 (4.2); 2.524 (5.3); 2.510 (104.6); 2.506(208.9); 2.502 (276.9); 2.497 (208.3); 2.470 (16.0); 2.333 (1.4); 2.328(2.1); 2.324 (1.5); 1.235 (0.4); 1.217 (5.4); 1.198 (11.4);1.179 (5.2);0.146 (1.2); 0.008 (10.9); 0.000 (280.5); −0.008 (14.3); −0.150 (1.3)Example 11: ¹H-NMR(400.0 MHz, DMSO): δ = 8.645 (13.2); 8.316 (0.4);8.167 (0.9); 8.157 (6.6); 8.152 (7.7); 8.144 (7.2); 8.141 (6.1);8.133(7.5); 8.121 (8.0); 8.103 (7.6); 7.603 (5.8); 7.576 (5.8); 7.560(2.1); 7.550 (16.0); 7.545 (14.9); 7.537 (9.2); 7.533 (9.0); 7.523(2.4); 7.509 (0.6); 7.157 (14.4); 7.155 (13.7); 5.756 (10.1); 4.312(0.4); 4.285 (1.3); 4.276 (0.8); 4.258 (1.6); 4.249 (2.1); 4.230 (0.8);4.221 (2.1); 4.194 (0.7); 4.169 (0.6); 4.142 (2.1); 4.115 (2.3); 4.106(1.6); 4.088 (1.0); 4.079 (1.4); 4.052 (0.5); 3.325 (90.4); 2.676 (0.6);2.671 (0.8); 2.666 (0.6); 2.524 (2.5); 2.511 (46.0); 2.506 (91.8); 2.502(120.2); 2.497 (88.0); 2.492 (56.7); 2.333 (0.7); 2.329 (1.0); 2.324(0.7); 0.146 (0.8); 0.008 (7.3); 0.000 (188.1); −0.009 (6.7); −0.150(0.8) Example 12: ¹H-NMR(400.0 MHz, DMSO): δ = 8.339 (6.7); 8.191 (3.5);8.184 (3.4); 7.704 (3.5); 7.700 (3.5); 7.445 (2.2); 7.425 (3.3); 7.353(2.3); 7.349 (2.2); 7.333 (1.5); 7.328 (1.4); 5.757 (1.0); 4.106 (1.3);4.080 (3.9); 4.054 (4.0); 4.029 (1.3); 3.324 (49.3); 2.670 (0.6); 2.502(92.9); 2.403 (16.0); 2.328 (0.6); 1.235 (0.7); 0.000 (5.1) Example 13:¹H-NMR(400.0 MHz, DMSO): δ = 8.089 (5.3); 7.990 (0.4); 7.489 (5.6);7.293 (4.3); 6.792 (0.4); 5.758 (0.4); 4.752 (0.3); 4.037 (0.8); 4.035(0.8); 4.012 (2.4); 4.009 (2.4); 3.986 (2.4); 3.983 (2.5); 3.960 (0.9);3.957 (0.9); 3.694 (0.4); 3.668 (0.4); 3.337 (15.5); 3.336 (16.9); 3.330(19.8); 2.525 (0.5); 2.520 (0.7); 2.511 (11.3); 2.507 (23.2); 2.502(30.8); 2.498 (22.6); 2.493 (11.3); 2.372 (15.1); 2.346 (0.6); 2.338(1.2); 2.329 (0.4); 2.291 (12.6); 2.204 (1.5); 2.154 (0.3); 2.145 (1.1);2.055 (0.5); 1.998 (14.2); 1.989 (16.0); 1.949 (0.4); 0.987 (0.4); 0.969(0.6); 0.008 (1.1); 0.000 (33.6); −0.009 (1.3) Example 14: ¹H-NMR(400.0MHz, DMSO): δ = 9.266 (0.3); 8.317 (0.9); 7.910 (3.2); 7.901 (2.2);7.485 (2.3); 7.474 (1.5); 7.189 (0.5); 7.013 (1.9); 6.999 (2.8); 4.310(0.5); 4.282 (0.5); 4.273 (0.6); 4.246 (0.6); 4.219 (0.3); 4.193 (0.6);4.184 (0.6); 4.166 (0.6); 4.157 (0.6); 3.913 (0.5); 3.886 (0.6); 3.876(0.5); 3.859 (0.3); 3.849 (0.5); 3.331 (519.1); 2.676 (1.9); 2.671(2.7); 2.667 (1.9); 2.662 (1.0); 2.524 (6.0); 2.520 (9.8); 2.511(146.3); 2.507 (304.5); 2.502 (406.6); 2.498 (299.7); 2.493 (148.9);2.435 (8.0); 2.424 (5.5); 2.375 (0.5); 2.338 (1.0); 2.333 (2.0); 2.329(2.8); 2.324 (2.2); 2.296 (1.6); 2.267 (0.5); 2.253 (1.8); 2.180 (6.0);2.109 (0.6); 2.091 (16.0); 1.351 (0.8); 1.259 (0.4); 1.233 (1.0); 0.008(1.3); 0.000 (44.6); −0.008 (1.8) Example 15: ¹H-NMR(400.0 MHz, DMSO): δ= 8.723 (10.3); 8.316 (0.5); 8.045 (9.4); 8.040 (7.0); 8.022 (16.0);7.211 (11.1); 5.756 (2.5); 4.184 (2.2); 4.159 (7.0); 4.146 (0.8); 4.133(7.3); 4.108 (2.5); 3.324 (132.3); 2.680 (0.4); 2.675 (0.7); 2.671(1.1); 2.666 (0.8); 2.662 (0.3); 2.524 (2.6); 2.519 (4.1); 2.511 (58.1);2.506 (118.2); 2.502 (156.8); 2.497 (112.2); 2.493 (52.3); 2.338 (0.4);2.333 (0.8); 2.328 (1.1); 2.324 (0.8); 2.319 (0.3); 1.235 (0.5); 0.146(0.7); 0.008 (5.7); 0.000 (174.4); −0.009 (5.5); −0.150 (0.7) Example16: ¹H-NMR(400.0 MHz, DMSO): δ = 10.306 (0.5); 8.725 (14.9); 8.597(0.3); 8.405 (0.4); 8.316 (0.7); 8.117 (0.4); 8.087 (9.3); 8.069 (9.3);7.945 (10.8); 7.921 (10.8); 7.698 (0.5); 7.672 (0.5); 7.214 (16.0);5.757 (2.3); 4.184 (3.3); 4.159 (10.5); 4.134 (10.9); 4.108 (3.7); 3.970(0.6); 3.943 (0.7); 3.918 (0.4); 3.640 (0.4); 3.326 (311.9); 3.295(0.5); 3.256 (0.4); 3.142 (0.3); 2.675 (1.5); 2.671 (2.0); 2.666 (1.5);2.541 (0.8); 2.524 (5.6); 2.510 (118.1); 2.506 (232.8); 2.502 (304.3);2.497 (223.3); 2.493 (110.3); 2.333 (1.5); 2.328 (2.0); 2.324 (1.5);1.178 (0.7); 1.160 (1.4); 1.143 (0.8); 0.008 (0.8); 0.000 (23.5); −0.009(0.9) Example 17: ¹H-NMR(400.0 MHz, DMSO): δ = 8.431 (5.6); 8.317 (0.7);7.891 (3.6); 7.885 (3.8); 7.640 (1.6); 7.635 (1.6); 7.620 (2.5); 7.614(2.4); 7.536 (3.2); 7.515 (2.2); 6.368 (4.8); 5.757 (0.3); 4.234 (0.8);4.224 (0.5); 4.206 (0.9); 4.197 (1.3); 4.178 (0.4); 4.169 (1.3); 4.142(0.5); 4.114 (0.4); 4.086 (1.3); 4.060 (1.4); 4.050 (0.9); 4.033 (0.5);4.023 (0.8); 3.325 (406.6); 2.675 (2.6); 2.671 (3.5); 2.666 (2.6); 2.575(1.8); 2.556 (4.7); 2.537 (5.8); 2.524 (9.7); 2.510 (199.9); 2.506(396.5); 2.502 (519.5); 2.497 (385.0); 2.493 (194.5); 2.444 (16.0);2.388 (0.7); 2.333 (2.4); 2.328 (3.3); 2.324 (2.5); 1.236 (0.6); 1.216(6.1); 1.198 (12.8); 1.179 (5.8); 0.008 (1.6); 0.000 (41.2); −0.008(1.5) Example 18: ¹H-NMR(400.0 MHz, DMSO): δ = 8.668 (9.3); 8.627 (0.8);8.323 (0.8); 8.304 (0.4); 8.148 (5.4); 8.129 (5.5); 7.768 (0.4); 7.742(0.4); 7.608 (4.6); 7.581 (4.6); 6.793 (10.6); 4.991 (0.5); 4.966 (0.6);4.287 (1.0); 4.252 (1.6); 4.224 (1.4); 4.196 (0.5); 4.124 (0.5); 4.098(1.5); 4.072 (1.7); 4.062 (1.4); 4.044 (0.9); 4.035 (1.2); 4.009 (0.4);3.330 (113.6); 2.750 (2.3); 2.679 (1.5); 2.510 (240.7); 2.488 (38.4);2.337 (1.6); 2.003 (7.4); 1.955 (16.0); 1.907 (8.3); 1.245 (0.3); 0.008(0.5) Example 19: ¹H-NMR(400.0 MHz, DMSO): δ = 20.012 (0.4); 8.317(2.9); 8.187 (2.7); 8.177 (1.9); 8.169 (2.9); 8.159 (1.7); 7.652 (2.2);7.644 (1.4); 7.626 (2.2); 7.617 (1.4); 7.054 (3.1); 7.047 (5.1); 4.385(0.8); 4.376 (0.4); 4.358 (0.9); 4.349 (1.0); 4.321 (1.1); 4.294 (0.4);4.285 (0.4); 4.258 (0.4); 4.248 (0.8); 4.221 (0.8); 4.200 (0.8); 4.173(0.9); 4.135 (0.4); 3.978 (0.4); 3.952 (1.1); 3.925 (1.1); 3.915 (0.9);3.899 (0.5); 3.888 (1.0); 3.861 (0.3); 3.330 (1595.1); 2.676 (5.4);2.671 (7.6); 2.667 (5.6); 2.524 (18.0); 2.511 (415.9); 2.507 (858.2);2.502 (1139.8); 2.498 (837.1); 2.493 (412.0); 2.481 (24.3); 2.475(14.3); 2.333 (5.5); 2.329 (7.6); 2.324 (6.3); 2.276 (9.6); 2.192(16.0); 1.351 (1.7); 1.298 (0.6); 1.258 (1.0); 1.233 (2.6); 1.161 (0.7);1.094 (0.4); 0.853 (0.4); 0.146 (0.6); 0.008 (4.2); 0.000 (127.6);−0.008 (4.2); −0.150 (0.6) Example 20: ¹H-NMR(601.6 MHz, DMSO): δ =19.975 (0.5); 9.713 (0.4); 9.694 (0.4); 9.573 (1.4); 8.411 (1.7); 8.393(1.6); 8.316 (0.6); 8.270 (3.8); 8.267 (3.8); 8.227 (1.1); 7.931 (5.2);7.508 (1.1); 7.358 (2.2); 7.293 (0.9); 7.133 (4.1); 7.112 (1.8); 6.375(1.0); 4.017 (0.5); 3.999 (1.6); 3.982 (1.6); 3.965 (0.6); 3.796 (1.2);3.778 (3.6); 3.761 (3.8); 3.744 (1.3); 3.326 (96.7); 2.614 (0.9); 2.523(1.5); 2.520 (1.9); 2.517 (1.9); 2.508 (56.6); 2.505 (124.1); 2.502(171.8); 2.499 (122.8); 2.496 (55.0); 2.386 (1.0); 2.370 (3.3); 2.330(15.7); 2.289 (6.9); 2.271 (3.0); 2.178 (7.7); 2.173 (16.0); 2.000(3.3); 1.351 (1.6); 1.336 (0.6); 1.259 (0.5); 1.249 (0.8); 1.228 (1.1);0.000 (1.9) Example 21: ¹H-NMR(400.0 MHz, DMSO): δ = 8.278 (5.3); 7.905(3.6); 7.639 (3.2); 7.634 (3.4); 7.414 (2.3); 7.393 (3.1); 7.291 (2.2);7.286 (2.1); 7.271 (1.6); 7.266 (1.6); 4.111 (1.3); 4.085 (3.9); 4.059(4.1); 4.034 (1.4); 3.325 (43.6); 2.671 (0.6); 2.666 (0.5); 2.506(67.0); 2.502 (88.0); 2.497 (66.3); 2.397 (16.0); 2.333 (0.5); 2.328(0.6); 2.324 (0.4); 1.998 (13.7); 1.235 (0.5); 0.000 (9.6); −0.008 (0.4)Example 22: ¹H-NMR(400.0 MHz, DMSO): δ = 8.618 (4.7); 7.885 (2.9); 7.867(2.9); 7.475 (2.6); 7.448 (2.5); 6.779 (5.4); 4.062 (1.2); 4.037 (3.9);4.011 (4.1); 3.985 (1.4); 3.322 (44.2); 2.675 (0.4); 2.671 (0.6); 2.666(0.4); 2.524 (1.4); 2.506 (65.8); 2.502 (88.0); 2.497 (66.2); 2.435(16.0); 2.333 (0.4); 2.328 (0.6); 2.324 (0.5); 1.997 (4.1); 1.949 (8.9);1.900 (4.7); 0.008 (0.3); 0.000 (10.4); −0.008 (0.5) Example 23:¹H-NMR(601.6 MHz, DMSO): δ = 8.182 (5.5); 7.500 (5.5); 7.281 (4.3);6.446 (5.7); 5.755 (0.4); 4.026 (0.6); 4.012 (1.7); 4.009 (1.8); 3.995(1.8); 3.992 (1.9); 3.974 (0.7); 3.326 (57.8); 2.613 (0.5); 2.523 (0.8);2.520 (1.0); 2.517 (1.0); 2.508 (29.7); 2.505 (65.1); 2.502 (90.5);2.499 (65.5); 2.496 (30.2); 2.391 (0.5); 2.386 (0.5); 2.361 (15.5);2.086 (0.7); 2.065 (0.4); 1.994 (16.0); 1.973 (0.8); 1.963 (1.3); 1.954(0.8); 1.950 (0.8); 1.941 (0.4); 1.398 (0.8); 0.991 (3.7); 0.987 (6.0);0.974 (3.2); 0.000 (1.0) Example 24: ¹H-NMR(400.0 MHz, DMSO): δ = 8.323(7.3); 8.305 (0.5); 7.838 (0.4); 7.749 (4.8); 7.736 (3.4); 7.578 (0.4);7.436 (2.5); 7.416 (3.6); 6.374 (4.0); 6.368 (3.3); 4.269 (0.5); 4.241(0.5); 4.232 (0.6); 4.205 (0.6); 4.151 (0.9); 4.125 (2.7); 4.098 (2.9);4.071 (1.0); 4.025 (0.7); 3.998 (0.7); 3.988 (0.5); 3.961 (0.5); 3.321(216.3); 2.680 (2.0); 2.675 (2.4); 2.671 (3.1); 2.594 (1.3); 2.576(3.8); 2.558 (4.0); 2.553 (3.5); 2.538 (2.3); 2.506 (357.6); 2.501(466.5); 2.497 (362.9); 2.418 (16.0); 2.355 (0.3); 2.328 (3.1); 2.324(2.5); 2.294 (0.4); 2.261 (0.4); 2.139 (1.3); 2.116 (13.5); 2.110(10.6); 1.227 (4.6); 1.222 (4.0); 1.208 (9.4); 1.204 (7.8); 1.190 (4.6);1.185 (3.8); 0.146 (2.7); 0.008 (26.2); 0.000 (549.3); −0.060 (0.4);−0.150 (2.8) Example 25: ¹H-NMR(400.0 MHz, DMSO): δ = 8.410 (5.2); 8.317(0.4); 7.998 (3.4); 7.981 (3.5); 7.649 (3.2); 7.644 (3.3); 7.418 (2.2);7.397 (3.0); 7.301 (2.2); 7.295 (2.2); 7.281 (1.6); 7.275 (1.6); 6.524(2.8); 6.522 (3.0); 6.507 (2.8); 6.505 (2.9); 4.117 (1.3); 4.091 (4.1);4.065 (4.3); 4.039 (1.5); 3.323 (115.5); 2.675 (1.1); 2.671 (1.6); 2.666(1.2); 2.524 (4.1); 2.519 (6.1); 2.510 (86.0); 2.506 (177.4); 2.501(236.9); 2.497 (175.3); 2.493 (87.2); 2.395 (16.0); 2.333 (1.1); 2.328(1.5); 2.324 (1.1); 1.989 (0.6); 1.175 (0.3); 0.146 (0.9); 0.008 (6.7);0.000 (210.8); −0.009 (7.6); −0.150 (0.9) Example 26: ¹H-NMR(400.0 MHz,DMSO): δ = 8.763 (13.6); 8.719 (1.6); 8.401 (0.9); 8.382 (0.9); 8.324(1.0); 8.227 (8.0); 8.209 (8.1); 7.782 (0.8); 7.755 (0.7); 7.617 (6.3);7.590 (6.3); 7.222 (16.0); 5.764 (2.6); 5.022 (0.3); 4.997 (1.1); 4.972(1.2); 4.948 (0.4); 4.323 (0.4); 4.295 (1.3); 4.260 (1.9); 4.232 (1.7);4.206 (0.6); 4.099 (0.6); 4.071 (1.6); 4.044 (1.9); 4.008 (1.3); 3.982(0.5); 3.331 (223.5); 2.753 (5.0); 2.683 (2.7); 2.679 (3.5); 2.675(2.8); 2.647 (0.4); 2.514 (411.2); 2.510 (530.6); 2.506 (403.1); 2.488(54.5); 2.341 (2.6); 2.337 (3.4); 2.332 (2.7); 1.243 (0.5); 1.223 (0.4);1.192 (0.5); 1.182 (0.3); 0.008 (1.2) Example 27: ¹H-NMR(400.0 MHz,DMSO): δ = 8.368 (5.6); 7.924 (3.6); 7.922 (3.7); 7.901 (3.7); 7.895(3.9); 7.652 (1.7); 7.646 (1.6); 7.631 (2.4); 7.626 (2.4); 7.542 (3.2);7.521 (2.2); 4.238 (0.9); 4.228 (0.5); 4.211 (1.0); 4.201 (1.4); 4.183(0.4); 4.174 (1.3); 4.147 (0.4); 4.113 (0.4); 4.086 (1.3); 4.076 (0.3);4.059 (1.4); 4.049 (0.9); 4.032 (0.5); 4.022 (0.9); 3.325 (76.1); 2.671(0.6); 2.666 (0.4); 2.524 (1.4); 2.510 (27.8); 2.506 (56.4); 2.501(76.0); 2.497 (58.1); 2.493 (30.0); 2.447 (16.0); 2.333 (0.3); 2.328(0.5); 2.324 (0.4); 2.010 (13.7); 1.351 (0.4); 1.298 (0.6); 1.259 (0.8);1.250 (0.5); 1.234 (1.2); 0.000 (0.5) Example 28: ¹H-NMR(400.0 MHz,DMSO): δ = 8.498 (5.4); 8.016 (3.8); 7.999 (3.9); 7.914 (3.6); 7.909(3.8); 7.659 (1.7); 7.653 (1.6); 7.638 (2.4); 7.633 (2.3); 7.546 (3.1);7.525 (2.2); 6.553 (3.0); 6.551 (3.2); 6.537 (2.9); 6.534 (3.1); 4.236(0.8); 4.226 (0.5); 4.209 (0.9); 4.199 (1.3); 4.181 (0.4); 4.172 (1.3);4.144 (0.4); 4.119 (0.4); 4.092 (1.3); 4.082 (0.3); 4.065 (1.5); 4.055(0.9); 4.038 (0.5); 4.028 (0.9); 3.345 (133.3); 3.341 (137.3); 3.290(0.3); 2.671 (0.5); 2.667 (0.3); 2.525 (1.2); 2.520 (1.8); 2.511 (26.1);2.507 (53.8); 2.502 (71.6); 2.498 (52.4); 2.493 (25.4); 2.448 (16.0);2.333 (0.3); 2.329 (0.5); 2.324 (0.3); 0.008 (1.9); 0.000 (59.6); −0.009(2.0) Example 29: ¹H-NMR(400.0 MHz, DMSO): δ = 8.736 (14.4); 8.316(2.3); 8.294 (10.4); 8.276 (10.4); 8.122 (9.5); 8.099 (9.5); 7.821(0.4); 7.197 (16.0); 5.756 (2.4); 4.421 (0.4); 4.392 (1.1); 4.357 (1.7);4.330 (1.5); 4.302 (0.6); 4.198 (0.9); 4.172 (2.5); 4.162 (1.1); 4.145(2.9); 4.136 (2.2); 4.118 (1.3); 4.109 (2.0); 4.081 (0.8); 3.323(659.7); 2.675 (3.6); 2.671 (4.8); 2.666 (3.7); 2.586 (0.4); 2.524(12.2); 2.510 (278.7); 2.506 (554.9); 2.502 (731.6); 2.497 (544.7);2.333 (3.6); 2.328 (4.9); 2.324 (3.7); 1.235 (0.8); 1.215 (0.4); 1.184(0.7); 1.167 (0.9); 1.151 (0.6); 0.146 (0.7); 0.008 (5.6); 0.000(164.4); −0.008 (7.6); −0.150 (0.8) Example 30: ¹H-NMR(400.0 MHz, DMSO):δ = 7.631 (4.9); 7.463 (0.3); 7.346 (3.9); 7.114 (0.6); 7.005 (4.8);4.070 (0.5); 4.056 (0.4); 4.045 (0.6); 4.031 (1.2); 4.006 (1.4); 3.983(1.3); 3.958 (1.3); 3.944 (0.6); 3.932 (0.5); 3.918 (0.6); 3.796 (0.5);3.769 (0.5); 3.330 (35.4); 2.675 (0.4); 2.671 (0.6); 2.666 (0.4); 2.524(1.3); 2.520 (2.1); 2.511 (32.6); 2.506 (68.1); 2.502 (92.3); 2.497(69.3); 2.493 (35.0); 2.375 (13.3); 2.345 (0.6); 2.330 (2.5); 2.182(0.4); 2.158 (2.4); 2.109 (16.0); 1.985 (13.8); 0.008 (1.6); 0.000(53.8); −0.009 (2.0) Example 31: ¹H-NMR(400.0 MHz, DMSO): δ = 8.403(4.2); 7.819 (2.3); 7.800 (2.3); 7.439 (2.0); 7.412 (2.0); 6.353 (4.5);4.078 (1.0); 4.053 (3.2); 4.027 (3.3); 4.001 (1.1); 3.338 (3.0); 3.333(9.2); 2.818 (0.4); 2.801 (1.0); 2.783 (1.4); 2.766 (1.1); 2.749 (0.4);2.511 (3.6); 2.507 (7.4); 2.503 (9.8); 2.498 (7.3); 2.494 (3.8); 2.425(11.8); 2.400 (0.4); 2.383 (0.7); 2.244 (0.7); 1.397 (1.1); 1.213(16.0); 1.195 (15.5); 0.984 (0.4); 0.000 (9.2); −0.008 (0.4) Example 32:¹H-NMR(400.0 MHz, DMSO): δ = 8.622 (4.9); 7.887 (2.9); 7.868 (2.9);7.475 (2.5); 7.448 (2.5); 6.982 (1.4); 6.847 (7.9); 6.712 (1.6); 5.756(1.9); 4.056 (1.3); 4.030 (3.9); 4.005 (4.1); 3.979 (1.4); 3.323 (47.5);2.675 (0.3); 2.671 (0.5); 2.666 (0.4); 2.524 (1.1); 2.510 (27.2); 2.506(56.2); 2.502 (75.5); 2.497 (56.6); 2.493 (28.9); 2.457 (0.5); 2.437(16.0); 2.333 (0.4); 2.328 (0.5); 2.324 (0.4); 2.086 (1.3); 0.008 (0.4);0.000 (11.8); −0.008 (0.5) Example 33: ¹H-NMR(400.0 MHz, DMSO): δ =8.650 (2.6); 8.627 (3.9); 8.414 (0.3); 8.317 (0.7); 8.098 (0.4); 7.958(3.9); 7.954 (5.4); 7.549 (0.4); 7.465 (2.4); 7.439 (3.5); 7.172 (6.7);7.162 (0.4); 5.757 (1.0); 4.303 (0.5); 4.276 (0.6); 4.266 (0.7); 4.239(0.7); 4.232 (0.3); 4.214 (0.4); 4.167 (0.6); 4.156 (0.5); 4.140 (0.7);4.130 (1.1); 4.103 (1.2); 4.081 (1.1); 4.054 (1.2); 4.045 (0.6); 4.027(0.5); 4.018 (0.6); 3.940 (0.6); 3.914 (0.7); 3.904 (0.6); 3.877 (0.5);3.331 (446.6); 2.692 (0.9); 2.676 (1.5); 2.671 (2.1); 2.666 (1.5); 2.591(1.1); 2.524 (5.0); 2.511 (114.9); 2.507 (234.5); 2.502 (309.1); 2.498(226.9); 2.493 (111.8); 2.428 (16.0); 2.333 (1.6); 2.329 (2.2); 2.324(1.7); 2.173 (1.0); 2.153 (12.5); 2.143 (8.7); 1.351 (0.6); 1.310 (0.4);1.293 (0.5); 1.259 (0.4); 1.234 (0.9); 1.184 (0.4); 1.175 (0.3); 0.008(1.1); 0.000 (36.2); −0.008 (1.4) Example 34: ¹H-NMR(400.0 MHz, DMSO): δ= 8.703 (12.7); 8.316 (1.1); 8.100 (10.6); 8.094 (10.9); 7.905 (5.5);7.884 (16.0); 7.866 (10.0); 7.861 (9.1); 7.845 (3.3); 7.839 (3.5); 7.137(13.3); 4.394 (0.7); 4.367 (2.5); 4.357 (1.2); 4.340 (2.8); 4.330 (3.5);4.313 (1.1); 4.303 (3.6); 4.276 (1.1); 4.165 (0.9); 4.139 (3.3); 4.129(0.9); 4.112 (3.7); 4.102 (2.7); 4.085 (1.4); 4.075 (2.7); 4.048 (0.9);3.325 (469.0); 3.303 (1.1); 2.679 (0.8); 2.675 (1.6); 2.671 (2.2); 2.666(1.6); 2.661 (0.8); 2.524 (5.7); 2.511 (122.2); 2.506 (248.6); 2.502(330.0); 2.497 (238.1); 2.493 (113.6); 2.337 (0.8); 2.333 (1.6); 2.328(2.2); 2.324 (1.6); 1.235 (0.4); 0.146 (2.2); 0.026 (0.5); 0.019 (1.1);0.008 (18.3); 0.000 (502.6); −0.009 (18.2); −0.023 (0.9); −0.032 (0.4);−0.150 (2.2) Example 35: ¹H-NMR(400.0 MHz, DMSO): δ = 8.317 (0.7); 8.251(4.6); 7.731 (4.5); 7.715 (3.1); 7.426 (2.2); 7.406 (3.1); 6.480 (4.1);6.479 (4.3); 6.474 (3.3); 6.472 (3.1); 4.264 (0.4); 4.237 (0.5); 4.228(0.6); 4.201 (0.6); 4.141 (0.7); 4.114 (2.4); 4.087 (2.5); 4.060 (0.9);4.023 (0.6); 3.996 (0.6); 3.986 (0.5); 3.959 (0.5); 3.362 (0.5); 3.330(358.6); 2.675 (2.0); 2.671 (2.5); 2.667 (1.6); 2.524 (4.8); 2.520(8.0); 2.511 (118.7); 2.507 (244.5); 2.502 (323.9); 2.498 (237.1); 2.493(116.6); 2.436 (0.6); 2.412 (16.0); 2.333 (1.6); 2.329 (2.2); 2.324(1.7); 2.133 (0.8); 2.110 (11.5); 2.102 (8.4); 1.997 (0.8); 1.983 (1.2);1.976 (1.2); 1.967 (0.9); 1.351 (0.6); 1.259 (0.4); 1.232 (0.9); 1.025(0.8); 1.004 (6.4); 1.000 (5.5); 0.991 (4.8); 0.988 (4.4); 0.980 (2.8);0.008 (1.1); 0.000 (38.4); −0.009 (1.4) Example 36: ¹H-NMR(400.0 MHz,DMSO): δ = 8.611 (5.0); 7.663 (5.8); 7.333 (4.5); 7.177 (5.7); 7.175(5.7); 5.757 (1.1); 4.037 (1.2); 4.011 (3.9); 3.985 (4.0); 3.959 (1.4);3.346 (5.5); 2.525 (0.5); 2.520 (0.8); 2.511 (12.0); 2.507 (24.8); 2.502(33.0); 2.498 (24.4); 2.493 (12.1); 2.470 (0.8); 2.411 (0.8); 2.383(15.2); 2.329 (0.7); 2.199 (0.4); 2.038 (16.0); 1.293 (0.4); 0.000 (8.6)Example 37: ¹H-NMR(600.1 MHz, CD₃CN): δ = 8.110 (0.3); 8.106 (0.3);8.012 (3.8); 7.598 (2.5); 7.586 (2.5); 7.499 (0.3); 7.486 (0.3); 7.264(2.1); 7.246 (2.1); 6.357 (4.7); 6.355 (4.5); 3.716 (0.8); 3.704 (0.6);3.629 (1.6); 3.625 (0.4); 3.612 (4.9); 3.608 (1.0); 3.596 (5.0); 3.592(1.0); 3.579 (1.7); 3.575 (0.4); 3.550 (0.3); 2.499 (16.0); 2.465 (0.9);2.456 (2.3); 2.411 (0.4); 2.133 (4.3); 1.955 (0.4); 1.951 (0.6); 1.947(4.5); 1.943 (8.1); 1.939 (11.9); 1.935 (8.0); 1.931 (4.0); 1.914 (0.4);1.906 (0.7); 1.900 (0.8); 1.893 (1.3); 1.885 (0.8); 1.879 (0.8); 1.871(0.4); 1.077 (0.5); 1.055 (0.6); 1.042 (1.8); 1.034 (2.2); 1.030 (3.3);1.026 (2.6); 1.022 (2.9); 1.017 (1.3); 1.012 (0.7); 1.005 (1.7); 1.000(2.9); 0.995 (2.2); 0.991 (1.4); 0.986 (3.1); 0.982 (1.7); 0.976 (0.6);0.974 (0.6); 0.000 (1.2) Example 39: ¹H-NMR(400.0 MHz, DMSO): δ = 8.250(5.3); 7.517 (5.6); 7.293 (4.5); 6.345 (4.6); 6.343 (4.7); 5.755 (4.4);4.048 (1.0); 4.023 (3.2); 3.997 (3.3); 3.971 (1.1); 3.321 (17.3); 2.579(1.3); 2.561 (3.8); 2.542 (4.0); 2.523 (2.0); 2.510 (14.4); 2.506(29.9); 2.501 (40.7); 2.497 (31.3); 2.493 (16.6); 2.370 (15.3); 2.328(0.3); 2.001 (16.0); 1.221 (5.8); 1.202 (12.4); 1.184 (5.6); 0.008(1.5); 0.000 (42.9); −0.008 (2.4) Example 40: ¹H-NMR(400.0 MHz, DMSO): δ= 8.412 (8.2); 8.193 (4.1); 8.186 (4.2); 7.981 (3.7); 7.976 (3.8); 7.699(1.7); 7.694 (1.7); 7.679 (2.3); 7.673 (2.3); 7.569 (3.1); 7.548 (2.3);4.254 (0.9); 4.244 (0.4); 4.227 (1.0); 4.217 (1.3); 4.199 (0.4); 4.190(1.3); 4.163 (0.4); 4.090 (0.4); 4.063 (1.2); 4.054 (0.4); 4.036 (1.4);4.027 (0.9); 4.009 (0.5); 4.000 (0.9); 3.325 (44.5); 2.670 (0.4); 2.524(1.3); 2.506 (50.5); 2.501 (65.8); 2.497 (48.8); 2.454 (16.0); 2.333(0.3); 2.328 (0.4); 2.324 (0.3); 1.236 (0.4); 0.000 (5.1) Example 41:¹H-NMR(400.0 MHz, DMSO): δ = 8.739 (14.3); 8.316 (2.9); 8.262 (11.1);8.243 (11.3); 8.228 (10.1); 8.205 (10.1); 7.839 (0.5); 7.814 (0.4);7.195 (16.0); 5.756 (6.3); 4.361 (0.4); 4.340 (1.0); 4.305 (1.5); 4.279(1.3); 4.179 (0.4); 4.154 (0.7); 4.128 (2.0); 4.101 (2.3); 4.092 (1.8);4.074 (1.1); 4.064 (1.6); 4.038 (0.6); 3.845 (2.2); 3.324 (955.8); 2.675(4.3); 2.671 (5.9); 2.666 (4.3); 2.662 (2.0); 2.524 (15.5); 2.511(332.6); 2.506 (669.9); 2.502 (882.7); 2.497 (635.7); 2.493 (303.8);2.337 (2.1); 2.333 (4.2); 2.328 (5.8); 2.324 (4.2); 2.086 (0.4); 1.257(0.6); 1.235 (0.9); 1.215 (0.4); 1.183 (0.4); 1.166 (0.3); 0.146 (1.0);0.008 (7.8); 0.000 (237.7); −0.009 (7.9); −0.150 (1.0) Example 43:¹H-NMR(400.0 MHz, DMSO): δ = 8.342 (5.7); 7.626 (3.4); 7.622 (3.5);7.404 (2.4); 7.384 (3.2); 7.277 (2.2); 7.273 (2.1); 7.257 (1.6); 7.253(1.6); 6.336 (5.1); 4.117 (1.2); 4.091 (3.8); 4.066 (3.9); 4.040 (1.3);3.326 (89.7); 2.671 (0.5); 2.560 (1.5); 2.541 (4.4); 2.522 (5.9); 2.506(62.9); 2.502 (80.4); 2.497 (60.3); 2.389 (16.0); 2.333 (0.4); 2.328(0.5); 1.212 (5.5); 1.193 (11.4); 1.174 (5.3); 0.000 (8.5) Example 44:¹H-NMR(400.0 MHz, DMSO): δ = 8.360 (5.0); 7.796 (2.9); 7.778 (2.9);7.438 (2.5); 7.411 (2.5); 6.398 (4.4); 5.757 (1.7); 4.059 (1.2); 4.033(3.9); 4.007 (4.1); 3.981 (1.4); 3.326 (68.0); 2.675 (0.4); 2.671 (0.6);2.666 (0.4); 2.524 (1.4); 2.511 (32.7); 2.506 (66.0); 2.502 (87.1);2.497 (64.1); 2.493 (31.8); 2.427 (16.0); 2.378 (0.4); 2.368 (0.6);2.333 (0.5); 2.329 (0.6); 2.324 (0.5); 2.268 (14.5); 2.066 (0.4); 0.000(5.8) Example 45: ¹H-NMR(400.0 MHz, DMSO): δ = 8.550 (2.5); 8.532 (3.5);7.854 (7.4); 7.460 (2.2); 7.437 (3.2); 6.766 (4.1); 6.760 (3.1); 4.292(0.4); 4.265 (0.5); 4.255 (0.6); 4.228 (0.6); 4.155 (0.4); 4.137 (0.5);4.128 (1.3); 4.102 (1.7); 4.076 (1.3); 4.068 (0.5); 4.049 (0.4); 4.040(0.3); 3.986 (0.5); 3.960 (0.6); 3.950 (0.5); 3.923 (0.5); 3.328 (8.8);2.505 (17.6); 2.501 (23.0); 2.497 (17.5); 2.428 (16.0); 2.144 (11.4);2.136 (8.4); 2.086 (3.4); 2.002 (3.4); 1.954 (7.2); 1.951 (6.5); 1.906(3.7); 1.903 (3.3); 0.000 (0.9) Example 46: ¹H-NMR(400.0 MHz, DMSO): δ =8.428 (5.0); 8.317 (0.4); 8.020 (3.1); 8.002 (3.1); 7.568 (2.4); 7.541(2.3); 6.422 (4.5); 4.259 (0.5); 4.251 (0.3); 4.232 (0.6); 4.223 (0.8);4.196 (0.8); 4.127 (0.9); 4.100 (1.0); 4.091 (0.7); 4.073 (0.4); 4.064(0.6); 3.328 (131.6); 2.729 (0.5); 2.676 (0.8); 2.671 (1.2); 2.666(0.9); 2.662 (0.4); 2.524 (2.8); 2.520 (4.2); 2.511 (60.6); 2.506(125.9); 2.502 (168.1); 2.497 (123.8); 2.493 (61.0); 2.468 (16.0); 2.338(0.4); 2.333 (0.9); 2.328 (1.6); 2.280 (14.4); 2.105 (0.4); 1.234 (0.4);0.008 (1.2); 0.000 (41.0); −0.009 (1.5) Example 47: ¹H-NMR(400.0 MHz,DMSO): δ = 8.642 (4.8); 7.721 (3.3); 7.716 (3.4); 7.444 (2.2); 7.424(3.3); 7.357 (2.5); 7.352 (2.4); 7.337 (1.6); 7.332 (1.6); 7.100 (5.1);4.098 (1.2); 4.073 (4.0); 4.047 (4.1); 4.021 (1.4); 3.324 (40.9); 2.671(0.4); 2.524 (0.9); 2.519 (1.4); 2.511 (20.0); 2.506 (41.1); 2.502(54.6); 2.497 (39.7); 2.492 (19.0); 2.400 (16.0); 2.333 (0.6); 2.328(0.5); 2.324 (0.3); 0.008 (1.8); 0.000 (55.9); −0.009 (1.9) Example 48:¹H-NMR(400.0 MHz, DMSO): δ = 8.317 (0.7); 8.166 (5.0); 8.055 (0.5);7.718 (5.2); 7.703 (3.7); 7.623 (0.4); 7.435 (2.6); 7.415 (3.6); 4.274(0.6); 4.247 (0.6); 4.237 (0.7); 4.210 (0.7); 4.149 (1.0); 4.140 (0.4);4.122 (3.0); 4.112 (0.5); 4.095 (3.1); 4.068 (1.1); 4.015 (0.7); 3.988(0.8); 3.978 (0.6); 3.951 (0.6); 3.354 (1.2); 3.328 (188.4); 2.680(0.7); 2.676 (1.1); 2.671 (1.4); 2.666 (1.1); 2.662 (0.6); 2.574 (0.3);2.524 (3.6); 2.520 (5.5); 2.511 (74.3); 2.506 (152.5); 2.502 (202.5);2.497 (147.9); 2.493 (71.9); 2.415 (14.9); 2.365 (1.2); 2.353 (0.8);2.338 (0.5); 2.333 (1.1); 2.329 (1.5); 2.324 (1.2); 2.319 (0.9); 2.307(12.9); 2.246 (1.2); 2.149 (0.8); 2.127 (0.3); 2.099 (15.7); 2.031(0.4); 2.007 (16.0); 1.234 (0.6); 1.031 (0.4); 1.013 (0.7); 0.995 (0.3);0.008 (1.5); 0.000 (51.5); −0.009 (1.7) Example 49: ¹H-NMR(400.0 MHz,DMSO): δ = 8.638 (2.3); 8.621 (3.3); 8.317 (0.7); 7.918 (4.8); 7.465(2.1); 7.439 (3.0); 7.132 (4.6); 4.301 (0.4); 4.273 (0.5); 4.263 (0.5);4.236 (0.5); 4.167 (0.4); 4.140 (0.5); 4.130 (1.0); 4.104 (1.0); 4.082(0.9); 4.055 (1.0); 4.046 (0.4); 4.028 (0.4); 4.019 (0.4); 3.946 (0.5);3.919 (0.6); 3.909 (0.4); 3.883 (0.5); 3.325 (200.0); 2.675 (1.7); 2.671(2.3); 2.666 (1.7); 2.524 (5.6); 2.506 (258.8); 2.502 (340.1); 2.497(251.2); 2.428 (16.0); 2.333 (1.8); 2.328 (2.4); 2.324 (1.8); 2.153(11.1); 2.146 (8.1); 0.146 (1.2); 0.008 (8.9); 0.000 (277.2); −0.008(10.7); −0.150 (1.3) Example 50: ¹H-NMR(400.0 MHz, DMSO): δ = 8.700(5.0); 8.316 (0.5); 8.011 (3.7); 8.005 (3.9); 7.698 (1.8); 7.692 (1.7);7.677 (2.4); 7.672 (2.4); 7.570 (3.1); 7.549 (2.3); 7.114 (5.2); 5.756(0.7); 4.259 (0.9); 4.249 (0.4); 4.232 (1.0); 4.222 (1.3); 4.205 (0.4);4.195 (1.3); 4.168 (0.4); 4.059 (0.3); 4.031 (1.2); 4.022 (0.4); 4.004(1.3); 3.995 (1.0); 3.977 (0.5); 3.968 (1.0); 3.941 (0.3); 3.324(164.1); 2.732 (0.6); 2.675 (0.9); 2.671 (1.2); 2.666 (0.9); 2.524(3.5); 2.510 (69.4); 2.506 (137.1); 2.501 (179.6); 2.497 (130.3); 2.493(62.9); 2.455 (16.0); 2.427 (0.4); 2.333 (0.9); 2.328 (1.2); 2.324(0.9); 2.301 (0.4); 0.008 (1.8); 0.000 (44.1); −0.009 (1.4) Example 51:¹H-NMR(400.0 MHz, DMSO): δ = 8.490 (4.8); 7.990 (0.4); 7.607 (5.7);7.385 (0.3); 7.320 (4.5); 6.753 (5.3); 5.756 (0.5); 4.049 (1.2); 4.024(3.9); 3.998 (4.0); 3.972 (1.4); 3.330 (31.0); 2.524 (0.5); 2.519 (0.8);2.511 (11.0); 2.506 (22.7); 2.502 (30.0); 2.497 (22.2); 2.493 (11.1);2.376 (15.2); 2.347 (0.6); 2.338 (1.2); 2.329 (0.4); 2.145 (1.1); 2.055(0.5); 2.027 (16.0); 2.002 (4.3); 1.954 (9.8); 1.906 (4.9); 0.987 (0.5);0.969 (0.7); 0.008 (1.7); 0.000 (48.0); −0.009 (2.0) Example 52:¹H-NMR(400.0 MHz, DMSO): δ = 8.460 (4.2); 8.038 (2.4); 8.020 (2.4);7.570 (1.9); 7.543 (1.9); 6.370 (4.5); 5.756 (15.0); 4.262 (0.4); 4.234(0.5); 4.225 (0.7); 4.198 (0.6); 4.131 (0.7); 4.104 (0.8); 4.095 (0.5);4.068 (0.5); 3.330 (14.1); 2.827 (0.4); 2.810 (1.0); 2.793 (1.4); 2.776(1.0); 2.759 (0.4); 2.524 (0.4); 2.511 (7.2); 2.507 (14.2); 2.502(18.4); 2.498 (13.7); 2.472 (11.8); 1.216 (16.0); 1.199 (15.6); 0.000(4.0) Example 53: ¹H-NMR(400.0 MHz, DMSO): δ = 8.714 (3.0); 8.680 (4.0);8.316 (0.7); 8.194 (9.3); 7.845 (3.3); 7.819 (4.4); 7.195 (4.5); 7.189(3.5); 5.756 (0.3); 4.401 (0.6); 4.374 (0.7); 4.364 (0.7); 4.337 (0.8);4.246 (0.7); 4.237 (0.4); 4.219 (0.8); 4.210 (1.1); 4.191 (0.4); 4.183(1.1); 4.156 (0.4); 4.071 (1.0); 4.044 (1.1); 4.035 (0.8); 4.018 (0.6);4.008 (0.8); 3.992 (0.7); 3.981 (0.5); 3.966 (0.8); 3.955 (0.7); 3.939(0.3); 3.929 (0.7); 3.324 (258.8); 2.739 (0.3); 2.675 (1.2); 2.671(1.6); 2.666 (1.2); 2.524 (4.5); 2.510 (90.1); 2.506 (181.6); 2.502(240.3); 2.497 (174.5); 2.493 (84.2); 2.469 (16.0); 2.333 (1.7); 2.328(2.0); 2.324 (1.3); 0.146 (1.5); 0.008 (12.7); 0.000 (335.6); −0.009(12.4); −0.027 (0.4); −0.150 (1.5) Example 54: ¹H-NMR(400.0 MHz, DMSO):δ = 8.663 (15.1); 8.316 (1.6); 7.888 (10.5); 7.882 (10.6); 7.732 (13.1);7.711 (15.4); 7.479 (8.1); 7.474 (7.8); 7.458 (6.9); 7.452 (6.8); 7.137(16.0); 4.221 (3.5); 4.196 (11.1); 4.170 (11.5); 4.145 (3.9); 3.324(386.1); 2.675 (2.6); 2.671 (3.5); 2.666 (2.6); 2.524 (9.9); 2.510(197.9); 2.506 (393.6); 2.502 (514.9); 2.497 (372.2); 2.493 (178.9);2.333 (2.5); 2.328 (3.3); 2.324 (2.4); 0.146 (1.8); 0.008 (15.3); 0.000(403.7); −0.009 (14.3); −0.150 (1.7) Example 55: ¹H-NMR(400.0 MHz,DMSO): δ = 8.668 (4.7); 8.315 (0.4); 8.147 (3.0); 8.128 (3.1); 7.598(2.2); 7.571 (2.2); 6.986 (1.3); 6.852 (5.3); 6.716 (1.6); 5.756 (0.3);4.275 (0.4); 4.249 (0.5); 4.240 (0.6); 4.213 (0.6); 4.092 (0.6); 4.065(0.7); 4.056 (0.6); 4.038 (0.3); 4.029 (0.5); 3.323 (140.2); 2.740(0.5); 2.679 (0.4); 2.675 (0.7); 2.671 (1.0); 2.666 (0.8); 2.661 (0.4);2.524 (2.4); 2.519 (3.7); 2.510 (55.7); 2.506 (116.1); 2.501 (156.5);2.497 (114.8); 2.492 (56.5); 2.478 (16.0); 2.333 (0.9); 2.328 (1.1);2.324 (0.8); 2.319 (0.4); 0.000 (0.4) Example 56: ¹H-NMR(400.0 MHz,DMSO): δ = 8.638 (2.4); 8.621 (3.4); 7.918 (5.0); 7.464 (2.1); 7.439(3.1); 7.131 (4.8); 4.300 (0.4); 4.273 (0.5); 4.263 (0.6); 4.236 (0.6);4.167 (0.4); 4.157 (0.3); 4.140 (0.5); 4.130 (1.0); 4.103 (1.1); 4.082(1.0); 4.055 (1.1); 4.045 (0.5); 4.028 (0.4); 4.018 (0.5); 3.945 (0.5);3.918 (0.6); 3.909 (0.5); 3.882 (0.5); 3.325 (56.3); 2.675 (0.5); 2.671(0.7); 2.666 (0.5); 2.524 (1.8); 2.510 (37.0); 2.506 (72.9); 2.502(95.9); 2.497 (71.3); 2.493 (35.6); 2.428 (16.0); 2.333 (0.5); 2.328(0.7); 2.324 (0.5); 2.153 (11.5); 2.145 (8.4); 0.146 (0.4); 0.008 (3.1);0.000 (80.1); −0.008 (3.4); −0.150 (0.4) Example 57: ¹H-NMR(400.0 MHz,DMSO): δ = 8.382 (5.0); 7.806 (2.9); 7.788 (2.9); 7.438 (2.5); 7.411(2.5); 6.368 (4.5); 6.366 (4.6); 5.756 (1.5); 4.066 (1.2); 4.041 (3.9);4.015 (4.1); 3.989 (1.4); 3.324 (45.7); 2.675 (0.4); 2.671 (0.5); 2.666(0.4); 2.574 (1.3); 2.555 (4.0); 2.536 (4.2); 2.510 (27.3); 2.506(54.9); 2.502 (73.2); 2.497 (55.5); 2.493 (29.3); 2.426 (16.0); 2.333(0.4); 2.328 (0.5); 2.324 (0.4); 1.213 (5.8); 1.195 (12.3); 1.176 (5.7);0.008 (1.9); 0.000 (50.4); −0.009 (2.8) Example 58: ¹H-NMR(400.0 MHz,DMSO): δ = 8.581 (5.7); 8.316 (0.5); 8.155 (0.4); 8.146 (2.6); 8.141(3.2); 8.133 (3.0); 8.122 (3.0); 7.889 (2.9); 7.871 (2.9); 7.555 (0.9);7.546 (6.6); 7.540 (6.3); 7.532 (3.9); 7.529 (4.1); 7.519 (1.1); 7.505(0.4); 7.473 (2.6); 7.447 (2.6); 7.132 (6.0); 5.756 (0.9); 4.079 (1.2);4.053 (3.8); 4.027 (4.0); 4.001 (1.4); 3.324 (139.4); 2.675 (0.8); 2.671(1.2); 2.666 (0.9); 2.506 (133.0); 2.502 (176.5); 2.497 (131.1); 2.446(16.0); 2.401 (0.4); 2.333 (0.9); 2.328 (1.2); 2.324 (1.0); 0.146 (1.0);0.008 (8.0); 0.000 (207.3); −0.008 (8.4); −0.150 (1.0) Example 59:¹H-NMR(400.0 MHz, DMSO): δ = 8.691 (4.6); 8.316 (0.3); 7.917 (6.2);7.676 (5.2); 7.203 (5.0); 5.756 (0.6); 4.116 (0.8); 4.112 (0.8); 4.104(0.3); 4.090 (2.3); 4.087 (2.3); 4.065 (2.3); 4.061 (2.3); 4.039 (0.8);4.035 (0.8); 3.324 (85.4); 2.675 (0.6); 2.671 (0.8); 2.666 (0.6); 2.524(2.2); 2.511 (43.3); 2.506 (85.9); 2.502 (112.3); 2.497 (81.1); 2.493(38.9); 2.406 (16.0); 2.364 (0.6); 2.333 (0.5); 2.328 (0.7); 2.324(0.5); 0.146 (0.4); 0.008 (3.1); 0.000 (86.6); −0.009 (3.2); −0.150(0.4)

Use Examples

1. Boophilus microplus—Injection Test

Solvent: dimethyl sulphoxide

To produce an appropriate active compound formulation, 10 mg of activecompound are mixed with 0.5 ml of solvent and the concentrate is dilutedwith solvent to the desired concentration.

1 μl of the active compound solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

The efficacy is assessed after 7 days by laying of fertile eggs. Eggswhich are not visibly fertile are stored in a climate-controlled cabinetuntil the larvae hatch after about 42 days. An efficacy of 100% meansthat none of the ticks has laid any fertile eggs; 0% means that all theeggs are fertile.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 20μg/animal: 2, 4, 5, 6, 9, 22, 26, 34, 47, 50, 53, 59

2. Meloidogyne Incognita Test

Solvent: 125.0 parts by weight of acetone

To produce an appropriate active compound formulation, 1 part by weightof active compound is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 20 ppm:18, 21, 33, 45, 55

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 20 ppm: 9,12, 18, 21, 26, 27, 30, 41, 55

3. Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound formulation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compound from the preparationexamples showed an efficacy of 100% at an application rate of 500 g/ha:2, 9, 44, 53, 55

In this test, for example, the following compounds of the preparationexamples showed an efficacy of 83% at an application rate of 500 g/ha:18, 34, 46

4. Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested by all stages of thegreenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that none of the spider miteshave been killed.

In this test, for example, the following compounds of the PreparationExamples showed an efficacy of 100% at an application rate of 500 g/ha:1, 2, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 26,29, 30, 31, 32, 33, 34, 36, 37, 39, 40, 41, 44, 45, 46, 47, 50, 51, 52,53, 54, 55, 57, 59

In this test, for example, the following compounds of the PreparationExamples showed an efficacy of 90% at an application rate of 500 g/ha:12, 24, 28, 35, 43, 48

5. Meloidogyne incognita Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2.5 parts by weight of alkylaryl poly glycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration, it being necessary to include the volume of soil which isdrenched in the calculation. It should be ensured that a concentrationof 20 ppm of emulsifier in the soil is not exceeded. To produce furthertest concentrations, water is used for dilution.

Pots filled with soil (loamy sand) are watered with the active compoundsolution. An egg/larvae suspension of the southern root-knot nematode(Meloidogyne incognita) is added, lettuce seeds are scattered over thesurface of the soil, and they are covered over with quartz sand. Thelettuce seeds germinate and the plants develop. The galls develop on theroots.

After 21 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls have been found; 0% meansthat the number of galls on the treated plants corresponds to theuntreated control.

In this test, for example, the following compounds of the PreparationExamples showed an efficacy of 85% at an application rate of 8 ppm: 2

6. Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water. If the addition of ammonium salts or/andpenetrants is required, these are each added in a concentration of 1000ppm to the formulation solution.

Bean plants (Phaseolus vulgaris) heavily infested by all stages of thegreenhouse red spider mite (Tetranychus urticae) are treated by sprayingwith the active compound formulation in the desired concentration.

After 7 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that none of the spider miteshave been killed.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 20 ppm:49, 56

Comparative Examples 1. Phaedon cochleariae—Spray Test (PHAECO)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound formulation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired period of time, the effect in % is determined. 100%means that all the beetle larvae have been killed; 0% means that nobeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples showed superior efficacy compared to4-[6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-(2,2,2-trifluoroethylsulphinyl)benzonitrileand5-fluoro-4-[6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-(2,2,2-trifluoroethylsulphinyl)benzonitrile:see Table 5 below.

2. Tetranychus urticae—Spray Test; OP-Resistant (TETHER)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce an appropriate active compound formulation, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested by all stages of thegreenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound formulation of the desired concentration.

After the desired period of time, the effect in % is determined 100%means that all the spider mites have been killed; 0% means that none ofthe spider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples showed superior efficacy compared to4-[6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-(2,2,2-trifluoroethylsulphinyl)benzonitrileand5-fluoro-4-[6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-(2,2,2-trifluoroethylsulphinyl)benzonitrile:see Table 5 below.

TABLE 5 Animal Substance Structure species Concentration % mortality dat4-[6-oxo-4- (trifluoromethyl)pyrimidin- 1-yl]-2-(2,2,2-trifluoroethylsulphinyl) benzonitrile

PHAECO TETRUR 500 g/ha  20 g/ha  0  0 7 dat 6 dat Example 2 according tothe invention

PHAECO 500 g/ha 100 7 dat Example 6 according to the invention

TETRUR  20 g/ha 100 6 dat 5-fluoro-4-[6-oxo-4- (trifluoromethyl)pyrimidin-1-yl]-2-(2,2,2- trifluoroethylsulphinyl) benzonitrile

PHAECO 500 g/ha  50 7 dat

The invention claimed is:
 1. Compound of the formula (I),

in which V represents oxygen; Q represents C—R⁵, where R⁵ representshydrogen, halogen, amino, cyano, nitro, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulphanyl, (C₁-C₆)-alkylsulphinyl,(C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphanyl,(C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,(C₃-C₆)-cycloalkyl or (C₁-C₆)-alkoxy; R³ and R⁶ independently of oneanother represent hydrogen, halogen, cyano or nitro; or represent(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylsulphanyl,(C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,(C₁-C₆)-alkylsulphanyl, (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,(C₁-C₅)-alkylcarbonyl, (C₁-C₅)-haloalkylcarbonyl or(C₂-C₆)-alkoxycarbonyl; or represent (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₃)-alkyl or (C₃-C₆)-cycloalkenyl, where theradicals mentioned above may optionally be substituted by halogen,alkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy; or representphenyl, heteroaryl, phenyl-(C₁-C₃)-alkyl or heteroaryl-(C₁-C₃)-alkyl,where the radicals mentioned above may optionally be substituted byhalogen, alkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy; orrepresent NR′R″, where R′ and R″ independently of one another representhydrogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₃-C₄)-alkenyl,(C₃-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₃-C₄)-alkynyl,(C₃-C₄)-haloalkynyl, (C₃-C₄)-cyanoalkynyl, (C₁-C₄)-alkylcarbonyl or(C₁-C₄)-alkoxycarbonyl; or where R′ and R″ together with the nitrogenatom to which they are attached may form an optionally halogen-, alkyl-,cyano-, nitro-, alkoxy-, haloalkyl- or haloalkoxy-substituted, saturatedor unsaturated three- to eight-membered ring optionally interrupted byone or more heteroatoms independently selected from the group consistingof O, S and N, with the proviso that two oxygen atoms must not bedirectly adjacent to one another; or W represents hydrogen or halogen; nrepresents the number 0 or 1; Y represents halogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or amino; or represents NR′″R″″,where R′″ and R″″ independently of one another represent hydrogen,(C₁-C₄)-alkyl or (C₂-C₄)-haloalkyl; X represents halogen, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl or (C₁-C₄)-alkoxy.
 2. Compoundaccording to claim 1, in which Q represents C—R⁵, where R⁵ representshydrogen, halogen, amino, cyano, nitro, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl or (C₁-C₄)-alkoxy; R³ and R⁶independently of one another represent hydrogen or halogen; or represent(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy;or represent (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₂)-alkyl,where the radicals mentioned above may optionally be substituted byfluorine, chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro,(C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy; or representphenyl or phenyl-(C₁-C₃)-alkyl, where the radicals mentioned above mayoptionally be mono- or disubstituted by fluorine, chlorine, bromine,iodine, (C₁-C₃)-alkyl, cyano, nitro, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkylor (C₁-C₃)-haloalkoxy; or represent heteroaryl selected from the groupconsisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, indolyl, isoindolyl and indazolyl, where the radicalsmentioned above may optionally be mono- or disubstituted by fluorine,chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro, (C₁-C₃)-alkoxy,(C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy; or represent NR′R″, where R′and R″ independently of one another represent hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphanyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylcarbonyl or(C₁-C₄)-alkoxycarbonyl; or where R′ and R″ together with the nitrogenatom to which they are attached may form a saturated four- tosix-membered ring which is optionally mono- or disubstituted byfluorine, chlorine, bromine, iodine, (C₁-C₃)-alkyl, cyano, nitro,(C₁-C₃)-alkoxy, (C₁-C₃)-haloalkyl or (C₁-C₃)-haloalkoxy and optionallyinterrupted by a heteroatom selected from the group consisting of O, Sand N; W represents hydrogen or fluorine; Y represents fluorine,chlorine, bromine, methyl, ethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, amino, methylamino or dimethylamino; X representsfluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl,methoxy or ethoxy.
 3. Compound according to claim 1, in which Qrepresents C—R⁵, where R⁵ represents hydrogen, methyl, ethyl, methoxy,cyclopropyl or trifluoromethyl; R³ and R⁶ independently of one anotherrepresent hydrogen, fluorine, methyl, ethyl, isopropyl, trifluoromethyl,pentafluoroethyl, difluoromethyl, 1,1-difluoroethyl,difluorochloromethyl, cyclopropyl or phenyl; W represents hydrogen orfluorine; Y represents fluorine, chlorine, bromine, methyl, or methoxy;X represents chlorine, fluorine or methyl.
 4. Compound according toclaim 1, in which Q represents C—R⁵, where R⁵ represents hydrogen ormethyl; R³ represents hydrogen, methyl, ethyl, cyclopropyl, isopropyl,difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl orphenyl; R⁶ represents hydrogen, fluorine or methyl; W representsfluorine; Y represents bromine, chlorine or methyl; X representschlorine, fluorine or methyl.
 5. Formulation, comprising at least onecompound of the formula (I) according to claim
 1. 6. Formulationaccording to claim 5, further comprising at least one extender and/or atleast one surface-active substance.
 7. Formulation according to claim 5,wherein the compound of the formula (I) is in a mixture with at leastone further active compound.
 8. Method for controlling one or morepests, comprising allowing a compound of the formula (I) according toclaim 1 to act on the pests and/or a habitat thereof, wherein the pestsare selected from the group consisting of ticks, spider mites, beetlesand southern root-knot nematodes.
 9. Method for protecting seed or agerminating plant from pests, comprising contacting seed with a compoundof the formula (I) according to claim 1, wherein the pests are selectedfrom the group consisting of ticks, spider mites, beetles and southernroot-knot nematodes.
 10. Seed obtained by a method according to claim 9.11. Compound according to claim 1, in which Q represents C—R⁵, where R⁵represents hydrogen, methyl, ethyl, methoxy, cyclopropyl ortrifluoromethyl; R³ and R⁶ independently of one another representhydrogen, fluorine, methyl, ethyl, isopropyl, trifluoromethyl,pentafluoroethyl, difluoromethyl, 1,1-difluoroethyl,difluorochloromethyl, cyclopropyl or phenyl; W represents hydrogen orfluorine; X and Y represent a combination (Y,X) selected from the groupconsisting of (Me,F), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F), (MeO,F),(Br,F), and (F,F).
 12. Compound according to claim 1, in which Qrepresents C—R⁵, where R⁵ represents hydrogen or methyl; R³ representshydrogen, methyl, ethyl, cyclopropyl, isopropyl, difluoromethyl,trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl or phenyl; R⁶represents hydrogen, fluorine or methyl; W represents fluorine; X and Yrepresent a combination (Y,X) selected from the group consisting of(Me,Cl), (Me,F), (Me,Me), (Cl,Cl), (Cl,F), and (Br,F).
 13. Methodaccording to claim 8, wherein the compound of formula (I) is applied tocrops and/or a habitat thereof.
 14. Method according to claim 8, whereinthe compound of formula (I) is administered to an animal.
 15. Compoundaccording to claim 1, wherein R⁵ represents halogen, amino, cyano,nitro, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulphanyl,(C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,(C₁-C₆)-haloalkylsulphanyl, (C₁-C₆)-haloalkylsulphinyl,(C₁-C₆)-haloalkylsulphonyl, (C₃-C₆)-cycloalkyl or (C₁-C₆)-alkoxy.